КАТАЛИТИЧЕСКАЯ СИСТЕМА НА ОСНОВЕ АЗОТИРОВАННОГО СМЕШАННОГО ОКСИДА И СПОСОБ ПОЛУЧЕНИЯ ЭТИЛЕН-НЕНАСЫЩЕННЫХ КАРБОНОВЫХ КИСЛОТ ИЛИ СЛОЖНЫХ ЭФИРОВ

Изобретение относится к способу получения α, β этилен-ненасыщенных карбоновых кислот или сложных эфиров, содержащему этапы, где вызывают контакт формальдегида или его подходящего источника с карбоновой кислотой или сложным эфиром формулы R-CH-COOR, где Rобозначает водород или алкильную группу, a Rобозначает водород, алкильную или арильную группу, в присутствии катализатора и возможно в присутствии спирта, где данный катализатор содержит азотированный оксид металла, имеющий, по меньшей мере, два типа катионов металлов Ми М, где Мвыбирают из металлов или металлоидов группы 3, 4, 13 (также называемой IIIA) или 14 (также называемой IVA) Периодической таблицы, и Мвыбирают из металлов металлоидов или фосфора группы 5 или 15 (также называемой VA) Периодической таблицы. Изобретение также относится к каталитической системе для реакции формальдегида или его подходящего источника с карбоновой кислотой или сложным эфиром формулы R-CH-COOR, где Rобозначает водород или алкильную группу, a Rобозначает ...

СПОСОБ ПОЛУЧЕНИЯ АЦИЛИРОВАННЫХ 1,3-ДИКАРБОНИЛЬНЫХ СОЕДИНЕНИЙ

Изобретение относится к усовершенствованному способу получения ацилированных 1, 3-дикарбонильных соединений, используемых в качестве агрохимикатов или промежуточных продуктов для производства агрохимикатов. Описано также получение соответствующих таутомерных форм ацилированных 1, 3-дикарбонильных соединений. Способ заключается в перегруппировке соответствующего сложного енольного эфира, причем эту перегруппировку проводят в присутствии азида щелочного металла. Способ позволяет устранить потребность в дорогостоящих выделении катализатора/реагента и системах обработки отходов. 6 з.п. ф-лы.

СПОСОБ ПОЛУЧЕНИЯ КАТАЛИЗАТОРА, КАТАЛИЗАТОР, ПОСРЕДСТВОМ НЕГО, И СПОСОБ ПОЛУЧЕНИЯ ЭТИЛЕННЕНАСЫЩЕННЫХ КАРБОНОВЫХ КИСЛОТ ИЛИ ЭФИРОВ

Настоящее изобретение относится к способам получения катализаторов. Предложен способ получения катализатора, включающий стадии: a) обеспечения непрокаленной пористой подложки из модифицированного металлом, где подложка из диоксида кремния имеет средний размер пор 2-1000 нм, где данная подложка из диоксида кремния содержит изолированные силанольные группы (-SiOH) в количестве ˂2,5 групп на нм2 и где металл-модификатор выбран из одного или более металлов из бора, магния, алюминия, циркония, гафния и титана, где металл-модификатор присутствует в виде моно- или динуклеарных частиц металла-модификатора; b) необязательно удаления любого растворителя или жидкого носителя из подложки на основе модифицированного диоксида кремния; c) необязательно сушки подложки на основе модифицированного диоксида кремния; d) обработки непрокаленной подложки на основе модифицированного металлом диоксида кремния каталитическим металлом, чтобы вызвать адсорбцию каталитического металла на подложке на основе модифицированного ...

ЧЕТЫРЕХЗАМЕЩЕННЫЕ БЕНЗОЛЫ

Изобретение относится к новым соединениям Формулы III или к его фармацевтически приемлемым солям, в которой: Rи Rнезависимо выбраны из группы, состоящей из: (a) H, (b) (C-C)алкила, (c) C-Cалкила, прерванного одной или более групп -O-, (d) (C-C)алкил-(C-C)циклоалкила и (e) (CH)Q, где n=1-2 и где Q обозначает ароматическую кольцевую систему, имеющую от 5 до 6 кольцевых атомов C, и причем Q может быть независимо замещен группами числом до 3, выбранными из галогена, при условии, что Rи Rодновременно не обозначают H, причем каждый алкил Rи Rможет быть независимо замещен одной или более групп, выбранных из группы, состоящей из галогена, гидрокси, циано, CFили C-Cалкила, или Rи Rвместе с углеродом, к которому они присоединены, образуют 3-7-членное циклоалкильное или 6-членное гетероциклоалкильное кольцо, включающее один атом кислорода и которое в случае необходимости несет C-Cалкильный заместитель, или Rи Rвместе с углеродом, к которому они присоединены, образуют 3-7-членное циклоалкильное кольцо ...

ПОЛУЧЕНИЕ ЭТИЛЕННЕНАСЫЩЕННЫХ КИСЛОТ ИЛИ ИХ ЭФИРОВ

Изобретение относится к усовершенствованному способу получения этиленненасыщенных кислот или их эфиров следующей формулы: R-C(=(CH))-COOR, где Rи R, каждый независимо, представляют собой водород или алкильную группу, и m равно 1, путем взаимодействия алкановой кислоты или эфира алкановой кислоты формулы R-CH-COOR, где Rи R, каждый независимо, представляют собой водород или алкильную группу с источником метилена или этилена формулы I, где Rи Rнезависимо выбраны из C-Cуглеводородных групп или Н; Х представляет собой О или S; n представляет собой целое число от 1 до 100; и m равно 1, в присутствии каталитической системы с получением в качестве продукта этиленненасыщенной кислоты или сложного эфира, где продукт в виде кислоты или сложного эфира затем приводят в контакт с диенофилом, чтобы устранить нежелательный цвет продукта, где диенофил представляет собой соединение формулы:где Z выбран из группы, состоящей из -C(O)Y, -CN, -NOили галогена; Y выбран из группы, состоящей из водорода, алкила ...

СПОСОБЫ И ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ ДЛЯ ПОЛУЧЕНИЯ ДИАЛКАНОВЫХ ЭФИРОВ, СОДЕРЖАЩИХ КОНЦЕВУЮ α,ω-ДИКАРБОНОВОКИСЛОТНУЮ ГРУППУ

КОМПЛЕКСЫ

КАТАЛИТИЧЕСКАЯ СИСТЕМА НА ОСНОВЕ АЗОТИРОВАННОГО СМЕШАННОГО ОКСИДА И СПОСОБ ПОЛУЧЕНИЯ ЭТИЛЕН-НЕНАСЫЩЕННЫХ КАРБОНОВЫХ КИСЛОТ ИЛИ СЛОЖНЫХ ЭФИРОВ

... 1. Способ получения этилен-ненасыщенных карбоновых кислот или сложных эфиров, предпочтительно α, β этилен-ненасыщенных карбоновых кислот или сложных эфиров, содержащий этапы, где вызывают контакт формальдегида или его подходящего источника с карбоновой кислотой или сложным эфиром в присутствии катализатора и возможно в присутствии спирта, где данный катализатор содержит азотированный оксид металла, имеющий, по меньшей мере, два типа катионов металлов Ми М, где Мвыбирают из металлов группы 2, 3, 4, 13 (также называемой IIIA) или 14 (также называемой IVA) периодической таблицы, и Мвыбирают из металлов группы 5 или 15 (также называемой VA) периодической таблицы.2. Способ по п.1, где азотированный оксид металла состоит из от двух до четырех катионов металла и анионов кислорода и азота.3. Способ по любому из пп.1 или 2, где металл типа Мвыбирают из одного или нескольких металлов в списке, состоящем из: - Be, Mg, Ca, Sr, Ba, Ra, B, Al, Ga, In, Tl, Sc, Y, La, Ac, Si, Ge, Sn, Pb, Ti, Zr, Hf и Rf ...

КАТАЛИЗАТОР НА ОСНОВЕ СМЕШАННЫХ ОКСИДОВ И СПОСОБ ПОЛУЧЕНИЯ КАРБОНОВЫХ КИСЛОТ ИЛИ СЛОЖНЫХ ЭФИРОВ С ЭТИЛЕНОВОЙ НЕНАСЫЩЕННОСТЬЮ

... 1. Катализатор для взаимодействия формальдегида или его подходящего источника с карбоновой кислотой или сложным эфиром для получения карбоновой кислоты или сложного эфира с этиленовой ненасыщенностью, предпочтительно карбоновых кислот или сложного эфира с этиленовой ненасыщенностью в α, β-положении, где катализатор включает оксид металла, имеющий, по меньшей мере, два типа катионов металла, Ми М, где Мпредставляет собой, по меньшей мере, один металл, выбранный из группы 3 или 4 в 4-6 периодах Периодической таблицы, группы 13 в 3-5 периодах Периодической таблицы, или остающихся элементов в лантаноидной группе (а именно, скандия, иттрия, лантаноидных элементов, титана, циркония, гафния, алюминия, галлия, индия), и Мпредставляет собой, по меньшей мере, один металл, выбранный из группы 5 в 5 или 6 периодах Периодической таблицы или группы 15 в 4 или 5 периодах Периодической таблицы (а именно, ниобия, тантала, мышьяка и сурьмы),в котором отношение М:Mнаходится в диапазоне от 10:1 до 1:10,и в ...

СПОСОБЫ ПОЛНОГО СИНТЕЗА РЕЗОЛВИНА E1

СПОСОБ СИНТЕЗА (Z)-3-[2-БУТОКСИ-3'-(3-ГЕПТИЛ-1-МЕТИЛУРЕИДО)БИФЕНИЛ-4-ИЛ]-2-МЕТОКСИАКРИЛОВОЙ КИСЛОТЫ

... 1. Способ синтеза (Z)-3-[2-бутокси-3'-(3-гептил-1-метилуреидо)бифенил-4-ил]-2-метоксиакриловой кислоты формулы (I) ! ! отличающийся тем, что сульфонат общей формулы (XII) ! , ! где R2 означает метил, трифторметил, фенил или толил, подвергают взаимодействию с 3-гептил-1-метил-1-[3-(4,4,5,5-тетраметил[1,3,2]диоксаборолан-2-ил)фенил]мочевиной формулы (IIIb) ! ! или с соответствующей бороновой кислотой формулы (IIIa) ! ! 2. Способ по п.1, отличающийся тем, что реакцию проводят в присутствии палладиевого или никелевого катализатора. ! 3. Способ по п.1 или 2, отличающийся тем, что сульфонат общей формулы (XII) ! ! получают омылением сложного эфира общей формулы (XIII) ! ! где R1 означает алкил. ! 4. Способ по п.3, отличающийся тем, что сложный эфир общей формулы (XIII) ! ! получают взаимодействием алкил (Z)-3-(3-бутокси-4-гидроксифенил)-2-метоксиакрилата общей формулы (XIV) ! ! с соединением, выбранным из трифлик ангидрида, мезилхлорида, бензолсульфонилхлорида и тозилхлорида. ! 5. Способ по п ...

Prepn. of acylated single carbon-hydrogen and cpds. - by acid deriv. in presence of calcium cpd., useful in prepn. of intermediates used in pharmaceuticals and plant protectives

Prepn. of ketones of formula (III) comprises reating a C-H acid cpd. of formula (I) with an acid deriv. of formula R4COX (II) in presence of a Ca cpd. of formula Can(R6)m (V). In the formulae R1-R3 = COOR', COR' SO2R', CN, NO2, halo or H; R' = alkyl; R4 = opt. substd. alkyl, cycloalkyl, alkenyl, alkynyl, X = a leaving gp.; n = 1 or 3; m = 1 or 2; R6 = halo, NO2, NO3, CN, SO4, BF4, S, PO4, ClO4 or R4COO. USE/ADVANTAGE - (III) are useful in prepn. of intermediates for use in prodn. of pharmacueticals and plant protectants. Reaction is quick and uses cheap and readily accessible Ca cpds.. Reaction takes place at 500m temp. in acetone (which is practically non-toxicds ...

1-Alkoxyhexatrien-2-carbonsäureester

Heterocyclische Carbene enthaltende Metallkomplexe als Katalysatoren für C-C-Verknüpfungen

Verfahren zur Herstellung von substituierten 3-Alkoxy-acrylestern

Verfahren zur Herstellung von Alkynylverbindungen.

VERFAHREN ZUR UMWANDLUNG EINER EINE ISOLIERTE C=C-DOPPELBINDUNG UND EINE FUNKTIONELLE GRUPPE ENTHALTENDEN VERBINDUNG GGF. IM GEMISCH MIT EINEM EINE ISOLIERTE C=C-DOPPELBINDUNG ENTHALTENDEN KOHLENWASSERSTOFF

VERFAHREN ZUM HERSTELLEN VON METHYLMETHACRYLAT

POLYAMINE UND IHRE THERAPEUTISCHE VERWENDUNG

KUPPLUNGSREAKTIONEN MIT PALLADIUMKATALYSATOREN

VERFAHREN ZUR HERSTELLUNG VON 1,3-DICARBONYLVERBINDUNGEN

Chemical processes

Complexes

Catalytic olefin metathesis reaction method

A method for performing an olefin metathesis or cross-coupling reaction is characterised by the catalyst system comprising: [a] a source of a d-block metal, such as Group VIII metal, iron, cobalt, copper, ruthenium, rhodium, nickel, palladium or platinum [b] optionally a promoter, an activator and/or a base, and [c] a source of a 3-membered carbocyclic ligand. Also disclosed is catalysing olefin metathesis or cross-coupling reactions, comprising the catalyst system and a method of producing the catalyst system wherein [b] optionally a promoter, an activator and/or a base is a further reagent.

Complexes

A palladium (II) complex of formula (1) or (3). R1 and R2 are organic groups having 1-20 carbon atoms or form a ring with E; R3, R4, R5, R6, R7, R8, R9, R10 and R11 is -H or an organic group having 1-20 carbon atoms; or R1/R3 or R2/R3 forms a ring and R4/R5, R5/R6, R7/R8, R8/R9, R9/R10 or R10/R11 may form a ring; R12 is an organic group having 1-20 carbon atoms; m is 0, 1,2,3,4 or 5; E is P or As; X is a non-coordinated anionic ligand; R18 and R19 are Me, -Et, -nPr, -iPr, -nBu, -iBu, cyclohexyl or cycloheptyl; R12 is an organic group having 1-20 carbon atoms; R20, R21, R22, R23 and R24 are H or organic groups having 1-20 carbon atoms; or one or both of R20/R21 or R22/R23 may form a ring. The complexes find use in carbon-carbon and carbon-heteroatom coupling reactions.

Production of ethylenically unsaturated acids or esters thereof

Cationic pi-allyl palladium complexes and their use in coupling reactions

A process for the production of ethylenically unsaturated carboxylic acids or esters

ORGANOMETALLIC COMPLEXES AND CHEMICAL PROCESS USING SAME

... 1,217,417. Organometallic complexes. NATIONAL DISTILLERS & CHEMICAL CORP. 5 July, 1968 [14 July, 1967; 17 July, 1967], No. 32314/68. Headings C2C and C2J. [Also in Division C5E] The invention comprises organometallic complexes of the formula where n is zero or an integer from 1 to 4; each R is selected from lower alkyl (C 1 -C 4 ) group, aryl group having from 6 to 16 carbon atoms, hydroxy group, nitro group, halide, dialkyl. amino, diarylamino and alkarylamino groups having 2 to 12 carbon atoms, or alkoxy or aryloxy group having 1 to 6 carbon atoms; M is Ru, Pt, Os, Pd, Ir, or Rh; Y is chloride bromide, nitrate, acetate, thiocyanate or cyanide group; A is -CR1 =N- (where R1 is hydrogen or an alkyl or aryl group having 1 to 10 carbon atoms), and Z is an alkyl group having 1 to 10 carbon atoms, aryl group or alkaryl, an alkoxy or aryloxy group having 1 to 10 carbon atoms, a hydroxy group, or an alkylamino, dialkylamino, arylamino or diarylamino group having 1 to 12 carbon ...

PROCESS FOR THE METATHESIS OF A CYCLIC OLEFIN AND AN ACRYLIC OLEFIN CARRYING A FUNCTIONAL GROUP

COMPOSITE INSECT ATTRACTANT FOR MALE WHITE-LINE DART MOTHS AND A PROCESS FOR PREPARING THE ACTIVE INGREDIENTS THEREOF

Production of unsaturated aliphatic esters

A catalyst containing manganese oxides supported on activated silica gel, suitable for condensations of formaldehyde with compounds containing hydrogen atoms activated by electron attracting groups, e.g. esters of aliphatic acids, is prepared by mixing silica gel particles (of size 80-200 mesh) with just enough of an aqueous solution of manganous acetate to wet the silica gel completely, allowing the mixture to stand for 1 hour, drying it overnight in an oven at 85-100 DEG C. and afterwards heating the dry particles in the fluidized state in a stream of air at 350 DEG C. for 1 hour. A catalyst comprising lead oxide on activated silica gel is prepared in a similar manner from lead acetate.ALSO:Esters of unsubstituted a ,b -unsaturated aliphatic monocarboxylic acids are made by the reaction in the vapour phase and at elevated temperature of formaldehyde and an ester of an unsubstituted saturated aliphatic monocarboxylic acid having at least two hydrogen atoms attached to the same carbon atom ...

Method for producing 4-oxoquinoline compound

Method for producing 4-oxoquinoline compound

Process and intermediates for preparing integrase inhibitors

Process and intermediates for preparing integrase inhibitors

Process and intermediates for preparing integrase inhibitors

Process and intermediates for preparing integrase inhibitors

Process and intermediates for preparing integrase inhibitors

Method for producing 4-oxoquinoline compound

Process and intermediates for preparing integrase inhibitors

Method for producing 4-oxoquinoline compound

Process and intermediates for preparing integrase inhibitors

Process and intermediates for preparing integrase inhibitors

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

SUBSTITUTED 1,3-DIPHENYLPROP-2-EN-1-ON DERIVATIVES, THEIR PRODUCTION AND APPLICATIONS

ZWIESTUFIGES PROCEDURE FOR THE PRODUCTION OF ORGANIC COMPOUNDS METHYL-BRANCHED OUT USING MORE DIMETHYLETHER AND HYDROGEN

PROCEDURE FOR THE PRODUCTION OF BETA KETOESTERVERBINDUNG

LANGKETTIGE INSATIATED ONES OXYGEN-CONTAINING CONNECTIONS AND THEIR USE WITHIN THE THERAPEUTIC, COSMETIC AND DIÄTETI RANGE

NEW SUBSTITUTED ARYL HEXADECIMAL SERVING ACIDS AND ESTERS OF IT, ITSELF FOR TREATMENT AND PREVENTION OF DIABETES, DYSLIPIDÄMIE AND ARTERIOSKLEROSE BEING SUITABLE, PHARMACEUTICAL COMPOSITIONS, THIS CONTAINING, AND PROCEDURE FOR THEIR PRODUCTION

PROCEDURE FOR the PRODUCTION OPTICAL of ACTIVE 2-Ä6 (HYDROXYMETHYL) - 1,3-DIOXAN-4-YLÜ-ESSIGSÄUREDERIVATE

PROCEDURE FOR the PRODUCTION OF 2,2-DIMETHYL-3 (1-PROPENYL) CYCLOPROPANCARBOXYLATESTER

VERFAHREN ZUR HERSTELLUNG NEUER THIAZOL- DERIVATE

AUSBAU

PROCEDURE FOR the PRODUCTION OF 6-Ä3 (1-ADAMANTYL) - 4-METHOXYPHENYLÜ-2-NAPHTOESÄURE

PROCEDURE FOR THE PRODUCTION OF NEW THIAZOL OF DERIVATIVES

PROCEDURE FOR THE PRODUCTION OF ADAPALENE

PROCEDURE FOR the PRODUCTION OF 2-DIHALOGEN VINYLCYCLOPROPANCARBONSAEUREESTERN

PROCEDURE FOR THE PRODUCTION OF NEW THIAZOL OF DERIVATIVES

PROCEDURE FOR the PRODUCTION OF (4E) - 5-CHLORO-2 ISOPROPYL-4-PENTENSÄUREESTER AND OPTICAL-ACTIVE ISOMER OF it

PROCEDURE FOR THE PRODUCTION OPTICAL OF ACTIVE ALPHAALKYLCARBONYLVERBINDUNGEN

PROCEDURE FOR the SYNTHESIS OF SUCCINYLOBERNSTERNSÄUREDIALKYLESTERN AND YOUR TRANSFORMATION IN DIALKYL 2,5-DIARYLAMINO-3,6 MORE DIHYDROTEREPHTHALSÄUREESTER

PROCEDURE FOR THE PRODUCTION OF PERFLUORALKYLALKOHOLEN.

MANUFACTURING PROCESS OF TRI FLUORINE METHYL CONNECTIONS.

PROCEDURE FOR THE PRODUCTION OF DIMETHYLCYCLOPROPANCARBONSÄURE.

DEVELOPMENT

PROCEDURE FOR THE PRODUCTION OF KETOVERBINDUNGEN

PRODUCTION OF '' GOSSYPLURE '' AND 1-METALLO-5,9 TETRADECADIEN.

PROCEDURE FOR the PRODUCTION OF SYMMETRICAL BICYCLO (3.3.0>OCTAN-DIONDICARBONSAEUREDIESTERN.

REAGENT AND PROCEDURE FOR PERFLUORALKYLIERUNG OF NUKLEOPHILEN SUBSTRATES BY NATRIUMPERFLUORALKANSULFINATE IN AN OXIDIZING MEANS

PROCEDURE FOR the SYNTHESIS the ALPHA SUBSTIUIERTEN AKRYLSÄUREN AND n (MERCAPTOACYL) AMINE ACIDS

PROCEDURE FOR THE PRODUCTION OF 2,4,6 TRIMETHYLPHENYLESSIGSÄURE

PROCEDURE FOR THE PRODUCTION OF AROMATIC OLEFINE

MANUFACTURING PROCESS TO the 2-CYCLOHEXYL-2-HYDROXY PHENYLESSIGSÄURE, INTERMEDIATE PRODUCT FOR it AND MANUFACTURING PROCESSES OF it

Procedure for the production of new 9 (5 ', 5 ' - Dimethylcyclopent-1' en-1' yl) - -3,7-dimethyl-nona-2,4,6,8-tetraenverbindungen

PROCEDURE FOR THE PRODUCTION OF INTERMEDIATE PRODUCTS

CHINONVERBINDUNGEN FOR THE TREATMENT OF DISEASES

CATALYTIC COMPOSITION AND PROCEDURE FOR ASYMMETRICAL ALLYLI ALKYLATION

PROCEDURE FOR THE C-ALKYLATION OF MALONIC ACID ESTERS

POLYMERIZE-CASH BIARYLE, PROCEDURE FOR THE PRODUCTION AND THEIR USE

PROCEDURE FOR THE PRODUCTION OF THE VALPROIN ACID

PERFLUOROSULFONYLMETHIDE CONNECTIONS; THEIR USE WITH THE PRODUCTION OF CC CONNECTIONS

PROCEDURE FOR THE PRODUCTION OF 2 - HYDROXY ACID ESTERS

PROCEDURE FOR THE PRODUCTION OF HYDROXY-25-ENE VITAMIN D CONNECTIONS

ALLYLI SUBSTITUTING REACTIONS

PROCEDURE FOR the PRODUCTION OPTICAL of ACTIVE 2 (6 - (HYDROXYMETHYL) - 1,3-DIOXAN-4-YL) - ACETIC ACID of DERIVATIVES

PROCEDURE FOR the PRODUCTION OF 2,7-DIMETHYL-2,4,6 OCTATRIENAL MONOACETALEN

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

NEW IMMUNOTHERAPEUTI MEANS AND THEIR USE IN THE REDUCTION OF CYTOKINENSPIEGEL

Process for the treatment of an ion exchange resin

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:— R 1 —C(═(CH 2 )—COOR 2 are also described.

Zeolite-palladium complex, method for producing the same, catalyst containing the complex, and method for producing a coupling compound by using the catalyst

There is provided a substance having much higher catalytic activity for a Suzuki-Miyaura coupling reaction than conventional heterogenous catalysts. The present invention provides a zeolite-palladium complex including USY-zeolite and Pd supported on the USY-zeolite, the Pd having a Pd—Pd coordination number of 4 or less and an oxidation number of 0.5 or less.

Method for synthesis of secondary alcohols

A method for synthesis of secondary alcohols is provided for pharmaceutical secondary alcohol by addition of organoboronic acids with aldehydes in presence of the cobalt ion and bidentate ligands as the catalyst. In addition, an enantioselective synthesis method for secondary alcohols is also herein provided in the present invention. The present invention has advantages in using less expensive cobalt ion and commercially available chiral ligands as the catalyst, wide scope of organoboronic acids and aldehydes compatible with this catalytic reaction and achieving excellent yields and/or enantiomeric excess.

Intermediate compounds and processes for the preparation of tapentadol and related compounds

The present invention discloses processes for the preparation of 3-[(1R,2R)-3-(dimethyl-amino)-1-ethyl-2-methyl-propyl]phenol (Tapentadol), salts thereof and related compounds of formula (A), including stereoisomers and pharmaceutically acceptable salts thereof, and to certain intermediates used in such process.

Process for Producing Aliskiren

A new route of synthesis of the compound Aliskiren of formula (I), used in the treatment of hypertension, is described.

METHOD FOR PRODUCING 1-AMINO-1-ALKOXYCARBONYL-2-VINYLCYCLOPROPANE

It is an object of the present invention to provide a novel method for producing (1R,2S)/(1S,2R)-1-amino-1-alkoxycarbonyl-2-vinylcyclopropane which is useful as a synthetic intermediate of therapeutic agents for hepatitis C and a synthetic intermediate thereof. According to the present invention, when a trans-2-butene derivative having a leaving group at each of the 1- and 4-positions is reacted with a malonic ester in the presence of a base, a specific amount of an alkali metal alkoxide or an alkali metal hydride is used as the base, and further a specific amount of a malonic ester is used to produce a cyclopropane diester, and further, chiral or achiral 1-amino-1-alkoxy-carbonyl-2-vinylcyclopropane and a salt thereof are synthesized using the cyclopropane diester. 3. The method according to claim 1 , which comprises a step of purifying the compound represented by the formula (4) after performing the step (i).5. The method according to claim 4 , wherein the step (vi) is a step (vi-1) of allowing the compound represented by the formula (4) claim 4 , which has been obtained by the step (v) claim 4 , to react with an enzyme claim 4 , cells containing the enzyme claim 4 , a preparation of the cells claim 4 , or a culture solution obtained by culturing the cells claim 4 , so as to produce an optically active compound represented by the formula (5).8. The method according to claim 4 , wherein the absolute stereochemistry of the compound represented by the formula (5) is (1S claim 4 ,2S).10. The method according to claim 9 , wherein claim 9 , in the step (vii-1) claim 9 , the reaction intermediate is allowed to react with a metal azide compound or a trialkylsilyl azide in the presence of an acid.11. The method according to claim 9 , wherein the absolute stereochemistry of the compound represented by the formula (5) is (1S claim 9 ,2S) claim 9 , and the absolute stereochemistry of each of the compounds represented by the formula (6) claim 9 , the formula (7) and the ...

PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-SUBSTITUTED-3-FORMYL-2-HYDROXYPROPANOIC ACID COMPOUND

The present invention provides a production method of optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound (4), which includes a step of reacting glyoxylic acid compound (1-1) or (1-2) with aldehyde (2) in the presence of optically active pyrrolidine compound (3); 2. The method of claim 1 , wherein the reaction is carried out in the presence of a solvent.3. The method of claim 2 , wherein the solvent is at least one selected from the group consisting of an aromatic hydrocarbon solvent claim 2 , an alcohol solvent claim 2 , a halogenated hydrocarbon solvent claim 2 , an ether solvent claim 2 , a nitrile solvent and water.4. The method of claim 1 , wherein the reaction is carried out within the range of 0-50° C.5. The method of claim 1 , wherein Ris a hydrogen atom.6. The method of claim 1 , wherein Ris a hydroxyl group claim 1 , and Arand Arare each independently a phenyl group optionally having C-Cfluorinated alkyl group(s).7. The method of claim 1 , wherein Ris a hydroxyl group claim 1 , and Arand Arare both 3 claim 1 ,5-bis(trifluoromethyl)phenyl groups.8. The method of claim 6 , wherein the absolute configuration of C** is S-configuration claim 6 , and the absolute configuration of C* is R-configuration.11. The method of claim 7 , wherein the absolute configuration of C** is S-configuration claim 7 , and the absolute configuration of C* is R-configuration. The present invention relates to a production method of an optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound.An optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound is known to be useful for, for example, as a drug substance or synthetic intermediate for a medicament, a pesticide and the like, or as a synthetic intermediate for vitamins such as pantothenic acid and the like.Concerning production method of an optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound, non-patent document 1 discloses a method of reacting ethyl glyoxylate ...

Surface Active Agents Derived from Biodiesel-Based Alkylated Aromatic Compounds

A surface active agent comprising an arylated methyl ester of a fatty acid, or mixture of fatty acids, derived from biodiesel or a triglyceride source is disclosed. The fatty acid mixture is condensed to methyl esters and alkylated with aromatic substituents under Friedel-Crafts conditions. The alkylated methyl esters may be alkoxylated using a catalyst derived from fatty acids, alkaline earth salts, and strong acids. The resulting nonionic surfactant may also be sulfonated to produce one class of anionic surfactants. The alkylated methyl esters may also be directly sulfonated to produce another class of anionic surfactants.

Synthesis and use of omega-3 and omega 6 very long chain polyunsaturated fatty acids (VLC-PUFA)

The invention provides methods of synthesizing omega-3 and omega-6 very long chain polyunsaturated fatty acids (VLC-PUFAs, C28-C42:4, 5 and 6), analogs and derivatives thereof, pharmaceutical compositions containing these isolated VLC-PUFA compounds and therapeutic uses therefor. 1. A method of coupling a long chain hydrocarbon to an extender hydrocarbon to form a very long chain hydrocarbon having at last 28 carbon atoms comprising:i. reacting a long chain hydrocarbon, having a nucleophillic displacement group on one end, with an extending reagent,ii. wherein the extending reagent comprises a nucleophillic attacking group and an extender hydrocarbon chain having a protecting functional group on one end, andiii. wherein the coupling is done in the presence of an activating catalyst.2. The method as recited in wherein the protecting functional group is selected from an ester and an ether.3. The method as recited in where the nucleophillic displacement group is a halogen.4. The method as recited in wherein the extending reagent is selected from a Grignard extender reagent and a zinc extender reagent.538-. (canceled)39. A method of lengthening a polyunsaturated fatty acid to form an ester comprising:a. reducing an ester of a first polyunsaturated fatty acid to form a primary alcohol;b. oxidizing the primary alcohol to form an aldehyde; andc. contacting the aldehyde with an extender reagent to form an elongated ester.40. The method of claim 39 , further comprising transesterifying a glyceride to form the first polyunsaturated fatty acid.4143-. (canceled)44. The method of claim 40 , wherein the glyceride is derived from an algae cultured in a fermentation medium.4561-. (canceled)62. The method of claim 39 , wherein the reducing is conducted in the presence of at least one of lithium aluminum hydroxide (LAH) and tetrahydrofuran (THF).6364-. (canceled)65. The method of claim 39 , wherein the oxidizing is conducted in the presence of at least one of dimethyl sulfoxide (DMSO ...

METHYLIDENE MALONATE PROCESS

An improved process for the production of methylidene malonates is attained by use of select iminium salt reactants. 2. The method of wherein R claim 1 , R claim 1 , Rand Rare each independently H or an alkyl claim 1 , aryl claim 1 , alkenyl or alkynyl.3. The method of wherein X is a halogen claim 1 , a non-nucleophilic anion claim 1 , and/or acidic anion.4. The method of wherein X is a halogen claim 1 , a carboxylate or a sulfonate.5. The method of wherein X is selected from chloride claim 1 , bromide claim 1 , iodide claim 1 , AsF claim 1 , SbF claim 1 , PF claim 1 , BF claim 1 , CHSO claim 1 , CFSO claim 1 , benzenesulfonate claim 1 , para-toluenesulfonate claim 1 , acetate claim 1 , propionate claim 1 , isobutyrate claim 1 , pivalate claim 1 , sufate claim 1 , bisulfate claim 1 , perchlorate claim 1 , SbCl claim 1 , SbCl claim 1 , and SnCl7. The method of wherein Rand Rare both hydrocarbon and/or heterohydrocarbon groups and represent a Cto Clinear or branched alkyl group claim 6 , a Cto Calicyclic group claim 6 , a Cto Calkenyl group claim 6 , or a Cto Calkynyl group claim 6 , either or both of which may be substituted with or contain an ether claim 6 , epoxide claim 6 , halo claim 6 , ester claim 6 , cyano claim 6 , aldehyde claim 6 , keto or aryl group.8. The method of wherein both Rand Rare hydrocarbon or heterohydrocarbon groups wherein at least one contains an ester linkage.11. The method of wherein Ris independently a Cto Clower alkyl and n is 1 or 2.12. The method of wherein the equivalent weight of iminium salt to malonic acid ester is from 1:1 to 10:1.13. The method of wherein the equivalent weight of iminium salt to malonic acid ester is from 1:1 to 6:1.14. The method of wherein the equivalent weight of iminium salt to malonic acid ester is from 1:1 to 4:1.15. The method of wherein the iminium salt is formed in-situ and the malonic acid ester is directly added to the iminium reaction product.16. The method of wherein the in-situ reaction involves an ...

Anti-tumor and anti-inflammatory dicinnamoyl-glycerol esters and their analogues

Synthetic dicinnamate compounds and their analogues are disclosed that exhibit anti-tumor activity and/or an anti-inflammatory activity, and have beneficial activity principally in destroying cancer cells. Furthermore, methods for the extraction of the extracts are disclosed.

Fluoroalkylation Methods And Reagents

A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.

Compound having hetero ring skeleton, and process for producing optically active compound using the aforementioned compound as asymmetric catalyst

The invention provides a compound having a heterocyclic skeleton of formula (I): wherein the substituents are as defined in the specification, as well as a tautomer thereof or a salt thereof. The invention also provides asymmetric synthesis methods involving the use of such a compound, tautomer thereof, or salt thereof, as a catalyst.

Catalyst for Producing Acrylic Acids and Acrylates

In one embodiment, the invention is to a process for producing an acrylate product. The process includes the steps of contacting an alkanoic acid and an alkylenating agent over a catalyst composition under conditions effective to produce the acrylate product. The catalyst composition comprises a metal phosphate matrix containing vanadium and bismuth. Preferably, the catalyst comprises, in an active phase, vanadium to bismuth at a molar ratio of at least 0.02:1. Preferably, the catalyst composition is substantially free of titanium.

System for Controlling the Reactivity of Boronic Acids

A protected organoboronic acid includes a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

SYNTHESIS OF METHYLENE MALONATES SUBSTANTIALLY FREE OF IMPURITIES

The present invention provides improved methods for the chemical synthesis of methylene malonates using the Knovenagel synthesis reaction. The method of the invention provides for improved methylene malonates by significantly reducing or eliminating the formation of alternative and/or deleterious side products, significantly reducing or eliminating unwanted consumption of methylene malonates, and significantly reducing or eliminating the degradation of methylene malonates. These advantages result in methylene malonates, which upon recovery, are of higher quality, greater purity, improved yield and possess overall improved performance characteristics (e.g., improved cure speed, retention of cure speed, improved shelf-life and/or stability). 158-. (canceled)59. A method of making a methylene malonate monomer comprising:(a) reacting a malonic acid ester with a source of formaldehyde in the presence of an acidic or basic catalyst and optionally in the presence of an acidic or non-acidic solvent, to form a reaction complex;(b) optionally, inactivating the catalyst; and(c) recovering methylene malonate monomer from the reaction complex.60. The method according to claim 59 , wherein inactivating the catalyst comprises forming an insoluble precipitate of the catalyst and removing the precipitate from the reaction mixture.61. The method according to claim 60 , wherein the precipitate is formed by reducing the solubility of the catalyst in the reaction mixture.62. The method according to further comprising:(d) minimizing the recovery of volatile latent acid forming impurities from the reaction complex.63. The method according to claim 62 , wherein the step of minimizing the recovery of volatile latent acid forming impurities comprises:(a) adding to the reaction mixture water and an acid having a pKa range of −8 to 5;(b) adding to the reaction mixture a sterically hindered organic acid; or(c) adding to the reaction mixture a non-volatile organic acid,or any combination of (a), ...

PREPARATION METHOD FOR FLUORINE-CONTAINING OLEFINS HAVING ORGANIC-GROUP SUBSTITUENTS

An object of the present invention is to provide a method that enables the easy and efficient (high yield, high selectivity, low cost) preparation of a fluorine-containing olefin substituted with an organic group or groups from a fluorine-containing olefin. 1. A method for preparing a fluorine-containing olefin substituted with an organic group or groups ,the method comprising a step of reacting a fluorine-containing olefin (excluding chlorotrifluoroethylene) with an organic boron compound in the presence of an organic transition metal catalyst containing at least one transition metal selected from the group consisting of nickel, palladium, platinum, rhodium, ruthenium, and cobalt.2. The method according to claim 1 , wherein the fluorine-containing olefin is an olefin substituted with one or more fluorine atoms.3. The method according to claim 1 , wherein the transition metal is at least one member selected from the group consisting of nickel and palladium.5. The method according to claim 4 , wherein R is an optionally substituted monocyclic claim 4 , bicyclic claim 4 , or tricyclic aryl.6. The method according to claim 4 , wherein at least one of fluorine atoms claim 4 , each of which is bonded to an sphybridized carbon atom of the fluorine-containing olefin claim 4 , is substituted with a group represented by R.7. The method according to claim 1 , wherein the step is performed in the presence of a base.8. The method according to claim 1 , wherein the step is performed in the absence of a base.9. The method according to claim 1 , wherein the organic transition metal catalyst is an organic nickel complex.10. The method according to claim 1 , wherein the organic transition metal catalyst is an organic palladium complex. The present invention relates to a method for preparing a fluorine-containing olefin substituted with an organic group or groups.1-Substituted fluorine-containing olefins, such as 1,1,2-trifluorostyrene, are useful for, for example, polyelectrolyte ...

ORGANOZINC COMPLEXES AND PROCESSES FOR MAKING AND USING THE SAME

Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions. The organozinc reagents are stable and, due to their high selectivity, permit maintenance of sensitive functional groups such as aldehydes during cross-coupling. 1. A process for making organozinc reagents comprising:(1) reacting (A) at least one organomagnesium complex or organozinc complex with (B) at least one coordinating compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex,(2) contacting an organic compound having at least one leaving group with magnesium metal and a zinc coordination complex ...

Process for the direct alpha-methylenation of ketones

The invention relates to a process for preparing an α-methylene ketone comprising the step of reacting a ketone with formaldehyde in the presence of a catalyst which is an organic compound comprising at least one acid function or the corresponding salt, ester or amide thereof and at least one amine function or the corresponding ammonium salt, or a zwitterion thereof.

DIRECT SYNTHESIS OF BIO-BASED ALKYL & FURANIC DIOL ETHERS, ACETATES, ETHER-ACETATES, AND CARBONATES

A method of preparing a glycol mono-ether or mono-acetate, or carbonate involving either one of two pathways from alkylene glycols, HMF or its reduction derivative products (i.e., FDM, bHMTHFs), is provided. In particular, according to one pathway, the alkylene glycol, HMF or FDM, bHMTHFs are reacted with a dialkyl carbonate in the presence of a deprotonating agent, in substantial absence of an extrinsic catalyst, to produce an ether, and subsequently reacting the ether with an acid base. According to the other pathway, alkylene glycols are reacted with an acetate donor in the presence of an acid, base, to generate an alkylene monoacetate, and etherified with a carbonate in the presence of a deprotonating agent. 1. A method of preparing a mono-ether from a diol compound , comprising either a first pathway or second pathway , wherein:{'sup': 1', '1', '1', '2', '2', '2, 'sub': '3', 'in the first pathway, the diol compound is contacted with an Rorganic acid in the presence of a Brønsted acid at a temperature and for time sufficient to form a Rmono ester of the diol compound, then the Rmono ester of the diol compound is contacted with a Ralkyl diester of the formula R(CO)Rin the presence of a deprotonating agent at a temperature and for a time sufficient to form the monoester ether; or'}{'sup': 2', '2', '2', '1, 'in the second pathway, the diol compound is contacted with the an Ralkyl diester of the formula R(CO3)Rin the presence of a deprotonating agent at a temperature and for a time sufficient to form a mono ester of the diol compound, then the mono ester of the diol compound is contacted with an Rorganic acid in the presence of a Brønsted acid at a temperature and for time sufficient to form the monoester ether;'}{'sup': 1', '2, 'wherein Rand Rare the same or different alkyl, cyclo-alkyl or aromatic moieties.'}2. The method according to claim 1 , wherein the diol compound is at least one member selected from the group consisting of ethylene glycol (EG) claim 1 , ...

Process for Preparing Pentenoate

The invention pertains to a process for preparing a compound of formula (1) 3. The process according to claim 2 , wherein step (c) is conducted in continuous mode.5. The process according to claim 4 , wherein step (d) is conducted in continuous mode.10. The process according to claim 8 , wherein step (d) is conducted in continuous mode.11. The process according to claim 9 , wherein step (d) is conducted in continuous mode. The present invention relates to processes for preparing pentenoate and pentenoate-like compounds. The invention further provides a process for preparing propenals.Synthetic routes for the preparation of pentenoate and pentenoate-like compounds are known in the art. Kelly et al (in Tetrahedron Letters, vol. 40, Iss. 16 (1999), pp. 3251-3254) discloses the synthesis of pentenoate by the reaction of bromo acetate derivatives and propenal derivatives in the presence of a Zinc-based catalyst. A further synthesis uses the condensation of acetate derivatives as described by Dewi-Wuelfling et al. (in Synlett, nb. 3 (2006), pp. 487-489). These reactions are exothermic and is consequently difficult to control and obtain high yields. Moreover, propenals, in particular acrolein, have a tendency to polymerize, rendering these compounds difficult to store and/or transport without substantial deterioration of the required propenal. Using such propenals to produce pentenoate or pentenoate-like compounds leads to an even lower yield and presence of (more) undesirable by-products.The objective of the present invention is to provide a novel process as well as an improved process to prepare pentenoate and pentenoate-like compounds.The present invention pertains to a process for preparing a compound of formula (1)wherein Ris independently chosen from C-Calkyl, cycloalkyl, aralkyl and aryl, and R, Rand Rare independently chosen from hydrogen and C-Calkyl, cycloalkyl, aralkyl and aryl;which process comprises the steps of:a) contacting a compound of formula (2)wherein ...

BENZOIC ACID COMPOUND AND METHOD FOR PREPARING THE SAME

A compound represented by formula I or II. X represents a mono substituent on a benzene ring, and is selected from —H, —I, —Br, —Cl, —F, —CN, an amino, and a derivative thereof; Ris a Calkyl, Calkyl substituted by cyclopropane or fluorine, except n-butyl; and M is an amine ion or metal ion. 2. The compound of claim 1 , wherein:X represents a mono substituent on a benzene ring, and is selected from —H, —I, —Br, —Cl, —F, —CN, an amino, and a derivative thereof;{'sub': 1', '3-5', '3-5, 'Ris a Calkyl, Calkyl substituted by cyclopropane or fluorine, except n-butyl; and'}M is an ion of K, Na, Ca, Zn or Mg.3. The compound of claim 1 , wherein X is Br or F; Ris a Calkyl claim 1 , Calkyl substituted by cyclopropane or fluorine claim 1 , except n-butyl; and M is an ion of K claim 1 , Na claim 1 , Ca.9. The compound of claim 8 , wherein a crystal of the compound 17 is polymorphic form A; under a Cu-Ka line claim 8 , λ=1.5418 Å claim 8 , an X-ray powder diffraction of the polymorphic form A under an diffraction angle 2θ is 6.10 claim 8 , 8.43 claim 8 , 10.36 claim 8 , 12.18 claim 8 , 13.34 claim 8 , 14.46 claim 8 , 15.30 claim 8 , 16.77 claim 8 , 17.93 claim 8 , 18.31 claim 8 , 18.60 claim 8 , 19.36 claim 8 , 20.16 claim 8 , 20.88 claim 8 , 21.30 claim 8 , 21.70 claim 8 , 22.10 claim 8 , 22.81 claim 8 , 23.18 claim 8 , 23.57 claim 8 , 24.37; a characteristic peak occurs at 6.88 claim 8 , and an error range of the diffraction angle 2θ is ±0.2.10. A method for treatment or relief of cerebral ischemia claim 1 , acute or chronic myocardial ischemia claim 1 , or amyotrophic lateral sclerosis claim 1 , the method comprising applying the compound of . This application is a continuation-in-part of International Patent Application No. PCT/CN2019/078059 with an international filing date of Mar. 14, 2019, designating the United States, now pending, and further claims foreign priority benefits to Chinese Patent Application No. 201810225467.4 filed on Mar. 19, 2018. The contents of all of ...

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I 110-. (canceled)13. The method of claim 12 , wherein the unsaturated fatty alcohol is the fatty olefin derivative.14. The method of claim 13 , wherein Ris methyl claim 13 , subscript y is 7 claim 13 , and subscript z is 3.16. The method of claim 15 , wherein Ris methyl claim 15 , subscript y is 7 claim 15 , subscript z is 3 claim 15 , and Ris acetyl.19. The method of claim 18 , wherein Ris H claim 18 , Ris methyl claim 18 , subscript y is 7 claim 18 , and subscript z is 3.21. The method of claim 20 , wherein:{'sup': '7a', 'Ris selected from the group consisting of alkyl, alkoxy, heteroalkyl, aryl, aryloxy, and heteroaryl, each of which is optionally substituted; and'}{'sup': '8a', 'X is O or S and Ris optionally substituted aryl; or'}{'sup': 8a', '12a', '13a', '14a, 'X is O and Ris CRRR.'}22. The method of claim 20 , wherein{'sup': '3a', 'Ris selected from the group consisting of 2,6-dimethylphenyl; 2,6-diisopropylphenyl;'}2,6-dichlorophenyl; and adamant-1-yl;{'sup': '4a', 'sub': 3', '2', '6', '5', '3', '3, 'Ris selected from the group consisting of —C(CH)CHand —C(CH);'}{'sup': '5a', 'Ris H;'}{'sup': '7a', 'Ris selected from the group consisting of pyrrol-1-yl; 2,5-dimethyl-pyrrol-1-yl; triphenylsilyloxy; triisopropylsilyloxy; 2-phenyl-1,1,1,3,3,3-hexafluoro-prop-2-yloxy; 2-methyl-1,1,1,3,3,3-hexafluoro-prop-2-yloxy; 9-phenyl-fluorene-9-yloxy; 2,6-diphenyl-phenoxy; and t-butyloxy; and'}{'sup': 8a', '8a, 'Ris R—X—, wherein'}X═O and{'sup': '8a', 'Ris phenyl which bears two substituents in the ortho positions with respect to O, or which bears at least three substituents, from which two substituents are in the ortho positions with respect to O and one substituent is in the para position with respect to O; or'}{'sup': '8a', 'Ris selected from the group consisting of optionally substituted 8-(naphthalene-1-yl)- ...

Polyvalent Vinyl Aromatic Compound and Method for Producing Same

A polyvalent vinyl aromatic compound represented by chemical formula (4) is produced by reacting (1) a specific vinyl aromatic compound and (2) a specific vinyl compound in the presence of (3-1) a metal complex and (3-2) a percarboxylic acid or a hypervalent iodine compound so that a vinyl group derived from the vinyl compound is introduced onto a carbon atom that is adjacent to the carbon atom to which a vinyl group is bonded in the vinyl aromatic compound. (In the formula, Ar represents a monocyclic aromatic hydrocarbon group or the like; R 1a represents a —CH 2 OC(═O)R 4 group or the like; R 2 represents a hydrogen atom or the like; R 3 represents a hydrogen atom or the like; A represents an alkyl group having 1-20 carbon atoms, or the like; and n represents an integer of 1-m.)

PROCESSES FOR THE PREPARATION OF ARGINASE INHIBITORS AND THEIR SYNTHETIC INTERMEDIATES

Provided herein are processes and intermediates useful for the preparation of certain compounds, including a compound of formula 21 or formula 22 2. (canceled)4. (canceled)6. (canceled)8. (canceled)10. (canceled)12. (canceled)14. (canceled)16. (canceled)18. (canceled)20. (canceled)22. (canceled)24. (canceled)26. (canceled)28. (canceled)30. (canceled)32. (canceled)34. (canceled)36. (canceled)38. (canceled)39. A process for preparing a compound of formula 2 as defined in claim 37 , the process comprising esterifying L-malic acid under suitable conditions to form the compound of formula 2 or a salt thereof.40. (canceled)42. (canceled)4463-. (canceled)65. (canceled)67. (canceled)69. (canceled)71. (canceled)73. (canceled)75. (canceled)7783-. (canceled)8594-. (canceled) Compounds of general formula 21 and formula 22including pharmaceutically acceptable salts thereof, exhibit potent arginase inhibition.U.S. Pat. Nos. 10,065,974 and 10,494,339 describe benchtop preparation of compounds of the general formula 21. U.S. Pat. No. 10,287,303 describes preparation of compounds of the general formula 22. A need exists for economical synthetic procedures and intermediate compounds for the preparation of the compounds of formula 21 and formula 22 including pharmaceutically acceptable salts thereof for batch process scale-up. Such alternative synthetic procedures and intermediate compounds are provided herein.Provided herein is a process for preparing a compound of formula 21:or a pharmaceutically acceptable salt thereof, wherein:Also provided herein is a process for preparing a compound of formula 22:or a pharmaceutically acceptable salt thereof, wherein:In some embodiments, the process for preparing a compound of formula 21 or formula 22 comprises treating a compound of formula 20or a salt thereof, wherein:In some embodiments, the suitable conditions to deprotect the compound of formula 20 comprise treating with hydrogen and a palladium catalyst.In some embodiments, the process for ...

PROCESS FOR PREPARING TAPINAROF

The present invention provides processes for the preparation of 3,5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3,5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3,5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same. 118.-. (canceled)20. The process of wherein X is Cl.21. The process of wherein the aromatizing comprises contacting the compound of Formula (II) or a salt thereof with quaternary ammonium salt in a solvent.22. The process of claim 21 , wherein the quaternary ammonium salt is tetraethylammonium chloride.24. The process of wherein the halogenating agent is selected from the group consisting of 1 claim 23 ,3-dichloro-5 claim 23 ,5-dimethylhydantoin; N-chlorosuccinimide; and trichloroisocyanuric acid.25. The process of claim 23 , wherein the halogenating is carried out in methanol and the halogenating agent is 1 claim 23 ,3-dichloro-5 claim 23 ,5-dimethylhydantoin.27. The process of claim 26 , wherein R is selected from the group consisting of methyl claim 26 , ethyl claim 26 , propyl claim 26 , or butyl.28. The process of claim 26 , wherein R is methyl or t-butyl.29. The process of claim 26 , wherein the cyclizing comprises contacting the compound of Formula (IV) or a salt thereof with potassium tert-butoxide in 2-methyltetrahydrofuran.31. The process of claim 30 , wherein the esterifying comprises heating the compound of Formula (V) or a salt thereof with aqueous hydrochloric acid in methanol.33. The process of claim 32 , wherein the decarboxylating comprises heating the compound of Formula (VI) or a salt thereof in the presence of triethylamine.35. The process of claim 34 , wherein each of Rand Ris ethyl.36. The process of claim 34 , wherein the hydrolyzing comprises treating the compound of Formula (VII) or a ...

PROCESS FOR PREPARING BIPHENYL COMPOUNDS

A process is provided for preparing a compound having the formula (I): 2. The process of claim 1 , wherein the water-miscible solvent is acetone.3Trametes versicolor.. The process of claim 1 , wherein the laccase is from4. The process of claim 1 , wherein the amount of laccase for one gram of compound of formula (II) is from 1.5 mg to 75 mg.5. The process of claim 1 , wherein the solution of the compound of formula (II) in a water-miscible solvent is prepared by adding said compound of formula (II) in said water-miscible solvent claim 1 , and adding a buffer solution.6. The process according to claim 5 , wherein the amount of water-miscible solvent is comprised between 5% and 10% of volume in comparison with the total volume of the mixture formed by said solvent and the buffer solution.7. The process of claim 1 , wherein the addition of an oxygen source according to a) is carried out for a sufficient time to saturate the solution in dissolved oxygen.8. The process of claim 1 , wherein the solution of the compound of formula (II) in the water-miscible solvent used for b) is saturated in oxygen.9. The process of claim 1 , wherein the pH of the solution of the compound of formula (II) in the water-miscible solvent is comprised between 4 and 7.10. The process of claim 1 , wherein step c) is a step of recovering the compound of formula (I) by centrifugation or filtration.11. The process of claim 1 , wherein the amount of laccase for one gram of compound of formula (II) is from 3 mg to 15 mg.12. The process of claim 5 , wherein the buffer solution is a sodium acetate buffer.13. The process of claim 7 , wherein the addition of an oxygen source according to step a) is carried out for 5 minutes. This application is a continuation of U.S. patent application Ser. No. 15/516,318, filed Mar. 31, 2017, which is a 371 application of International Application PCT/EP2015/072957, filed Oct. 5, 2015, and which claims the benefit of European Patent Office application Serial No. ...

PROCESS FOR RUTHENIUM-CATALYZED TRANSVINYLATION OF CARBOXYLIC ACIDS

The invention relates to a process for transvinylation of a carboxylic acid feedstock with a vinyl ester feedstock to obtain a vinyl ester product and the corresponding acid of the vinyl ester feedstock in the presence of one or more ruthenium catalysts, wherein a) the vinyl ester feedstock, the carboxylic acid feedstock and a ruthenium catalyst are fed to the reactor, and b) the transvinylation reaction is carried out, characterized in that a carbonyl-free Ru(III) carboxylate is used as the ruthenium catalyst and in that no carbon monoxide is supplied, c) the reaction is carried out at a temperature of 110 to 170° C., d) upon completion of the transvinylation reaction, the vinyl ester feedstock and the corresponding acid are separated from the reaction mixture by distillation, e) the vinyl ester product is separated by distillation from the bottom product of the distillation, and f) the remaining reaction mixture is recycled into the reactor. 1. A process for transvinylation of a reactant carboxylic acid with a reactant vinyl ester to afford a product vinyl ester and the corresponding acid of the reactant vinyl ester in the presence of one or more ruthenium catalysts , whereina) the reactant vinyl ester, the reactant carboxylic acid and a ruthenium catalyst are supplied to the reactor, andb) the transvinylation reaction is performed,whereinthe ruthenium catalyst employed is a carbonyl-free Ru(III) carboxylate and no carbon monoxide is supplied,c) the reaction is performed at a temperature of 110° C. to 170° C.,d) after completion of the transvinylation reaction the reactant vinyl ester and the corresponding acid are distillatively removed from the reaction mixture, ande) the product vinyl ester is distillatively removed from the bottoms product of the distillation, andf) the remaining reaction mixture is recycled into the reactor.2. The process as claimed in claim 1 , wherein the residence time in the reaction zone is 0.25 to 5 hours.3. The process as claimed in ...

METHOD FOR PRODUCING ORGANIC COMPOUND

Provided is a method for producing an organic compound, the method making it possible to ensure an adequate reaction time and obtain a targeted substance at a high yield even in an organic reaction that requires a relatively long time to complete the reaction. A method for producing an organic compound, wherein the method is characterized in that: a fluid processing apparatus F used in the production method is equipped with an upstream processing unit that processes a fluid to be processed between at least two processing surfaces and that relatively rotate, and a downstream processing unit disposed downstream of the upstream processing unit, the downstream processing unit being provided with a plurality of labyrinth seals that function to retain and stir the fluid to be processed that has been processed by the upstream processing unit; due to the fluid to be processed, which contains at least one type of organic compound, being passed through the upstream processing unit, the fluid to be processed is subjected to upstream processing; due to the fluid to be processed that has been subjected to upstream processing being passed through the downstream processing unit, the fluid to be processed that has been subjected to upstream processing is subjected to downstream processing; and the upstream processing and the downstream processing are performed continuously. 1. A method for producing an organic compound , whereina fluid processing apparatus used in the production method comprises an upstream-side processing part in which a fluid to be processed is processed between at least two processing surfaces that rotate relative to each other, and a downstream-side processing part is arranged in the downstream side of the upstream-side processing part and is provided with a plurality of labyrinth seals having functions of retaining and stirring the fluid to be processed being processed in the upstream-side processing part, whereinby the fluid to be processed which contains at ...

Synthesis of pheromones and related materials via olefin metathesis

Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.

Integrated Process for the Production of Acrylic Acids and Acrylates

A process for producing an acrylate product from methanol and acetic acid, in which, in a reaction zone A, the methanol is partially oxidized to formaldehyde in a catalyzed gas phase reaction, the product gas mixture A obtained and an acetic acid source are combined to form a reaction gas input mixture B which comprises acetic acid in excess over formaldehyde, and the formaldehyde in reaction gas input mixture B is aldol-condensed to acrylic acid in the presence of a catalyst in a reaction zone B to form an acrylic acid-containing product gas mixture B from which an acrylate product stream may be separated. Suitable aldol condensation catalysts include vanadium-bismuth, vanadium-titanium-bismuth, vanadium-bismuth-tungsten, vanadium-titanium-tungsten, vanadium-titanium and vanadium-tungsten.

DILUTE CHEMICAL REACTION PROCESS

Disclosed is a process for carrying out a cyclisation reaction, a polymerization reaction, an enzymatic reaction showing substrate inhibition, an enzymatic reaction showing product inhibition, a reaction showing precipitation of the substrate or of a reactant, the process comprising the steps of 261062. The process according to claim 1 , wherein the first filtration membrane () has a rejection of at least one compound selected from the reaction product claim 1 , catalyst and one or more of the reactants which are caused to react with the substrate of 60-95% claim 1 , and wherein the at least one compound is returned from the retentate side () of the first filtration membrane () to the reactor ().36. The process according claim 1 , wherein the first membrane () has a substrate rejection of at least 95%.4. (canceled)55277222172. The process according to wherein the diluting substrate feed system () for supplying substrate to the reactor () comprises a second filtration membrane () which is permeable to the solvent (S) claim 1 , wherein the permeability of the second filtration membrane () for the substrate (X) is selected such that the permeate (P) of the second membrane has a desired concentration of the substrate (X) in the solvent (S) claim 1 , wherein permeate (P) with the desired concentration of the substrate (X) in the solvent (S) is supplied from the permeate side () of the second filtration membrane () to the reactor ().67207887. The process according to claim 5 , wherein the second filtration membrane () comprises a retentate side () claim 5 , and substrate (X) which is rejected by the second filtration membrane () is supplied to a substrate feed tank () and is further mixed with solvent claim 5 , and wherein a mixture containing solvent and substrate is supplied from the substrate feed tank () to the second filtration membrane ().711687. The process according to claim 5 , comprising the returning of solvent (S) from the permeate side () of the first ...

PROCESS FOR THE SYNTHESIS OF (2E, 4E, 6Z, 8E)-8-(3,4-DIHYDRONAPHTHALEN-1(2H)-YLIDENE)-3,7-DIMETHYLOCTA-2, 4, 6-TRIENOIC ACID

This invention relates to a novel method for the synthesis of (2E,4E,6Z,8E)-8-(3,4-dihydronaphthalen-1(2H)-ylidene)-3,7-dimethylocta-2,4,6-trienoic acid. In particular, the invention relates to several improvements in several individual steps of the multi-step synthesis scheme 1. A method for the synthesis of MRZ-20321 comprising one or more of the steps of:(a) synthesizing E-2/Z-2 by performing a bromination of 1 in a solvent selected from benzotrifluoride and 1,3-bis(trifluoromethyl)benzene, particularly benzotrifluoride;(b) lithiating 1;(c) adding tetralone to lithiated 1;(d) synthesizing Z-7 starting from Z-5, wherein said method comprises the step of synthesizing the methyl ester Z-6;(e) reducing Z-6 to obtain Z-7;(f) oxidizing Z-7 with stabilized 2-iodoxybenzoic acid (SIBX);(g) reacting Z-8 with E-3/Z-3 in the presence of a lithium dialkylamide, particularly lithium diisopropylamide or lithium diethylamide, particularly lithium diisopropylamide; and/or(h) recrystallizing MRZ-20321 from isopropanol or from n-heptane or from mixtures of n-heptane and 2-methyl tetrahydrofuran.2. The method of claim 1 , wherein step (a) is performed in benzotrifluoride as solvent.3. The method of or claim 1 , wherein said bromination in step (a) is performed with N-bromosuccinimide.4. The method of claim 3 , wherein said bromination is performed by using a radical initiator selected from azobisisobutyronitrile claim 3 , and dibenzoyl peroxide claim 3 , particularly azobisisobutyronitrile.5. The method of any one of to claim 3 , wherein said lithiating in step (b) is performed by using a lithiating reagent selected from a lithium dialkylamide claim 3 , particularly lithium diisopropylamide or lithium diethylamide; a lithium claim 3 , sodium or potassium salt of bis(trimethylsilyl)amide (HMDS) claim 3 , particularly lithium bis(trimethylsilyl)amide; and lithium tetramethylpiperidine.6. The method of any one of to claim 3 , wherein said step (d) comprises reacting Z-5 with a ...

METAL-CATALYZED COUPLING OF ARYL AND VINYL HALIDES WITH ALPHA, ALPHA-DIFLUOROCARBONYL COMPOUNDS

The coupling of aryl, heteroaryl, and vinyl halides with α,α-difluoroketones or silyl ethers or siylenol ethers of α,α-difluoroketones and α,α-difluoroamides and esters are described. Further derivatization of the coupling products (such as ketone cleavage and Baeyer-Villiger oxidation) is also described. 2. The composition according to claim 1 , wherein said complex is present in said composition in an amount of less than 10 mol % relative to said α claim 1 ,α-difluoromethyl carbonyl compound.3. The composition according to claim 2 , wherein said complex is present in said composition in an amount of about 2 mol % to about 5 mol % relative to said α claim 2 ,α-difluoromethyl carbonyl compound.5. The composition according to claim 4 , wherein said complex is present in said composition in an amount of less than 10 mol % relative to said silyl enol ether.6. The composition according to claim 5 , wherein said complex is present in said composition in an amount of about 2 mol % to about 5 mol % relative to said silyl enol ether.76. The composition according to any one of - claims 4 , wherein said composition does not contain BuSnF.87. The composition according to any one of - claims 4 , wherein said composition does not contain an organotin reagent.98. The composition according to any one of - claims 4 , wherein R claims 4 , R claims 4 , and Rare independently selected from unsubstituted C claims 4 , C claims 4 , C claims 4 , C claims 4 , Cand Calkyl.10. The composition according to claim 9 , wherein one or more of R claim 9 , R claim 9 , and Rare methyl.11. The composition according to any preceding claim claim 9 , further comprising a solvent.12. The composition according to claim 11 , wherein said solvent is a non-polar claim 11 , organic solvent.13. The composition according to claim 12 , wherein said solvent is toluene.14. The composition according to any preceding claim claim 12 , wherein said base is a member selected from CsCOand KPO.17. The composition ...

PROCESSES AND INTERMEDIATES FOR PREPARING alpha,omega-DICARBOXYLIC ACID-TERMINATED DIALKANE ETHERS

The present disclosure provides a process for the preparation of compounds of formula (III), 2. The process of claim 1 , further comprising the step of performing an aqueous work-up of the solution of step (b) to isolate an organic solution of the compound of formula (III).3. The process of claim 1 , further comprising the step of treating the crude compound of formula (III) with an aqueous solution of a hydroxide or oxide of an alkali or earth alkaline metal.5. The process of claim 1 , further comprising the step of removing the organic layer by evaporation to afford crude crystalline α claim 1 ,ω-dicarboxylic acid-terminated dialkane ether salt of formula (IV) in the form of an alcohol solvate or hydrate claim 1 , wherein the alcohol solvate or hydrate is stirred with tetrahydrofuran with subsequent addition of one or more anti-solvents to obtain the crystalline form of the α claim 1 ,ω-dicarboxylic acid-terminated dialkane ether salt of formula (IV).6. The process of claim 1 , further comprising the step of adding one or more anti-solvents so that the salt of the α claim 1 ,ω-dicarboxylic acid-terminated dialkane ether of formula (IV) is insoluble.7. The process of claim 1 , further comprising the step of humidifying the precipitate to obtain a crystalline salt of a α claim 1 ,ω-dicarboxylic acid-terminated dialkane ether of formula (IV).9. The process of claim 1 , comprising treating a solution of a compound of formula (III) in a water-miscible solvent with an aqueous solution of a base claim 1 , wherein the water-miscible solvent is selected from DMSO claim 1 , DMF claim 1 , methanol claim 1 , isopropyl alcohol claim 1 , and ethanol; or treating a solution of a compound of formula (III) in a water-immiscible solvent with an aqueous solution of a base claim 1 , wherein the water-immiscible solvent is selected from toluene claim 1 , xylene claim 1 , methyl ethyl ketone claim 1 , and methyl isobutyl ketone. This application is a continuation of U.S. application ...

GAS PHASE PRODUCTION OF ALKYL ALKANOATES

An alkane-containing stream is reacted to produce an alkene, which is carbonylated to produce an alkyl alkanoate, e.g., methyl propanoate, by a gas phase process comprising the step of contacting under carbonylation conditions the alkene, e.g., ethylene, carbon monoxide, an alkanol, e.g., methanol, and a solid sulfide-based metal catalyst. 1. A process comprising: (a) providing a gas feed stream comprising >1 mol % of an alkane; (b) at least partially converting the alkane to produce a gaseous first intermediate stream comprising water , unreacted alkane , and >1 mol % of an alkene; (c) removing the majority of the water from the gaseous first intermediate stream to produce a gaseous second intermediate stream comprising at least one alkene; and (d) contacting under gas phase carbonylation conditions the gaseous second intermediate stream , carbon monoxide gas , an alkanol gas and a solid sulfide-based metal catalyst to produce an alkyl alkanoate.2. The process of comprising: (a) providing a gas feed stream comprising >1 mol % of an alkane; (b) at least partially converting the alkane to produce a gaseous first intermediate stream comprising water claim 1 , other hydrocarbons claim 1 , H claim 1 , CO claim 1 , CO claim 1 , unreacted alkane claim 1 , and >1 mol % of an alkene; (c) removing the majority of the water from the gaseous first intermediate stream to produce a gaseous second intermediate stream comprising at least one alkene claim 1 , other hydrocarbons claim 1 , H claim 1 , CO claim 1 , COand unreacted alkane; and (d) contacting under gas phase carbonylation conditions the gaseous second intermediate stream claim 1 , carbon monoxide gas claim 1 , an alkanol gas and a solid sulfide-based metal catalyst to produce an alkyl alkanoate.3. The process of wherein the alkene is of the formula CHin which n is from 2 to 12 claim 1 , and the alkanol comprises from 1 to 30 carbon atoms.4. The process of wherein the alkane is methane and the alkene is ethylene.5. The ...

METHOD FOR PREPARING 3-TRIFLUOROMETHYL CHALCONES

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein Mis Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is ORor NRR, and R, Rand Rare as defined in the disclosure. Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above. 1. A compound which is 1-chloro-3-iodo-5-(trifluoromethyl)benzene. This invention pertains to a method for preparing 3-trifluoromethyl chalcones and trifluoroacetyl intermediates. The present invention also relates to novel trifluoroacetyl and halo compounds useful as starting materials and intermediates for the aforedescribed method.The present invention provides a method for preparing a compound of Formula 1whereinZ is optionally substituted phenyl; andQ is phenyl or 1-naphthalenyl, each optionally substituted;comprising distilling water from a mixture comprising a compound of Formula 2a compound of Formula 3a base comprising at least one compound selected from the ...

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions. 1. A method of forming a borylated arene comprising:providing a substrate comprising a substituted arene ring comprising from 1 to 4 substituents, wherein the arene ring is unsubstituted at a first position that is electronically favored for CH-activation and unsubstituted at a second position that is sterically favored for CH-activation; andcontacting the substrate with an iridium precursor complex, a ligand chosen from a monodentate ligand and a bidentate ligand, and a borylation reagent under conditions effective to form a first borylated arene and optionally a second borylated arene;wherein the first borylated arene comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the first position,wherein the second borylated arene, when formed, comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the second position, andwherein the molar ratio of the first borylated arene to the second borylated arene is at least 1:1, as determined by GC-FID.2. The method of claim 1 , wherein the arene ring comprising from 1 to 3 substituents.3. The method of claim 1 , wherein the arene ring is substituted with an electron withdrawing group selected from the group consisting of —F and —CF.4. The method of claim 1 , wherein the substrate comprises a phenyl ring substituted with an electron withdrawing group selected from the group consisting of —F and —CF claim 1 , unsubstituted in a position ortho to the electron withdrawing group claim 1 , and unsubstituted in a position meta to the electron withdrawing group claim ...

Dehydration of water containing source of formaldehyde, and a method for producing an ethylenically unsaturated carboxylic ester

Disclosed are methods for dehydrating a water containing source of formaldehyde in which water is separated from the water containing source of formaldehyde using a zeolite membrane. In certain aspects, the water containing source of formaldehyde includes a separation enhancer having a relative static permittivity ranging from 2.5 to 20, and the water containing source of formaldehyde may further include methanol. In certain aspects, (meth)acrylic acid alkyl ester may be produced using the dehydrated source of formaldehyde.

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions. 1. A method of forming a borylated arene comprising:providing a substrate comprising a substituted arene ring comprising from 1 to 4 substituents, wherein the arene ring is unsubstituted at a first position that is electronically favored for CH-activation and unsubstituted at a second position that is sterically favored for CH-activation; andcontacting the substrate with an iridium precursor complex, a ligand chosen from a monodentate ligand and a bidentate ligand, and a borylation reagent under conditions effective to form a first borylated arene and optionally a second borylated arene;wherein the first borylated arene comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the first position,wherein the second borylated arene, when formed, comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the second position, andwherein the molar ratio of the first borylated arene to the second borylated arene is at least 1:1, as determined by GC-FID.2. The method of claim 1 , wherein the arene ring comprising from 1 to 3 substituents.3. The method of claim 1 , wherein the arene ring is substituted with an electron withdrawing group selected from the group consisting of —F and —CF.4. The method of claim 1 , wherein the substrate comprises a phenyl ring substituted with an electron withdrawing group selected from the group consisting of —F and —CF claim 1 , unsubstituted in a position ortho to the electron withdrawing group claim 1 , and unsubstituted in a position meta to the electron withdrawing group claim ...

PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE

The invention relates to processes for preparing (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside and compositions comprising the same. 2. The process of claim 1 , wherein said reacting is carried out in the presence of a Lewis acid.3. The process of claim 2 , wherein said Lewis acid is TMSOTf.4. The process of claim 3 , wherein said reacting is carried out in the presence of activated molecular sieves.5. The process of claim 1 , wherein said cleaving is carried out in the presence of Hand Pd/C in MeOH.6. The process of claim 1 , wherein said separation procedure is carried out using preparative thin layer chromatography.7. The process of claim 1 , wherein said deprotecting is carried out in a solution of NaOMe and MeOH.9. The process of claim 8 , wherein said reducing agent is lithium aluminum hydride (LAH) in THF.11. The process of claim 10 , wherein said benzylating agent is BnBr and NaH.13. The process of claim 12 , wherein said reducing agent is Hand Pd/C.15. The process of claim 14 , wherein said Stobbe condensation reaction is carried out in MeOH and in the presence of lithium.16. The process of claim 15 , wherein said lithium is in the form of lithium wires.17. The process of claim 14 , wherein said esterification reaction is carried out with MeOH in the presence of HSO.18. The process of claim 14 , wherein said compound of formula (4) is prepared by the process comprising reacting vanillin with methyl succinate via a Stobbe condensation reaction claim 14 , followed by an esterification reaction.19. The process of claim 18 , wherein said Stobbe condensation reaction is carried out in MeOH and in the presence of lithium wires.20. The process of claim 18 , wherein said esterification reaction is carried out with MeOH in the presence of HSO.22. The process of claim 21 , wherein said reacting of step (a) is carried out in the presence of TMSOTf.23. The process of claim 22 , wherein said reacting of step (a) is carried out in the ...

RUTHENIUM POLYMERISATION CATALYSTS

Cis and trans ruthenium complexes that can be used as catalysts for ring opening metathesis polymerisation (ROMP) are described. The complexes are generally square pyramidal in nature, having two anionic ligands X. Corresponding cationic complexes where one or both of the anionic ligands X are replaced by a non-co-ordinating anionic ligand are also described. Polymers such as polydicyclopentadiene (PDCPD) can be prepared using the catalysts. 3. The method according to wherein the group A is an N-heterocyclic carbene.4. The method according to wherein the anionic ligands X are independently selected from the group consisting of halogen claim 1 , benzoate claim 1 , C-Ccarboxylates.5. The method according to wherein the groups Rand Rare H and aryl.6. The method according to wherein the groups Rand Rare fused to form a substituted or unsubstituted indenylidene moiety.8. The method according to wherein the anionic ligands X are independently selected from the group consisting pivalate claim 1 , trifluoroacetate claim 1 , C-Calkoxy claim 1 , phenoxy claim 1 , C-Calkyl thio claim 1 , tosylate claim 1 , mesylate claim 1 , brosylate claim 1 , trifluoromethane sulfonate claim 1 , phenylacetate claim 1 , and pseudo-halogen.10. The method according to wherein the groups Rand Rare fused together to form a ring that may be substituted or unsubstituted claim 9 , saturated or unsaturated and may be fused to a further ring.11. The method according to wherein the groups Rand Rare fused to form a substituted or unsubstituted indenylidene moiety.12. The method according to wherein the group A is an N-heterocyclic carbene.14. The method according to wherein Rand Rare aryl.15. The method according to wherein Rand Rare phenyl.16. The method according to wherein Ris selected from the group consisting of substituted or unsubstituted primary alkyl and substituted or unsubstituted aryl.16. The method according to wherein Ris methyl claim 9 , ethyl or phenyl.17. The method of claim 1 , further ...

METHOD FOR SYNTHESIZING A PRECURSOR OF A SINGLE DAIRY-LACTONE ISOMER

This disclosure provides a method for preparing a precursor of a single dairy-lactone isomer, methods of preparing a single dairy-lactone isomer, and to the organoleptic uses thereof. 6. The method according to claim 5 , wherein the dotted line of said molecule of formula (III) represents a single carbon-carbon bond obtained by hydrogenating an α claim 5 ,β-unsaturated lactone.7. The method according to claim 5 , wherein said molecule of formula (III) is obtained by oxidizing a dihydrolevoglucosenone in the presence of a peracid claim 5 , followed by hydrolysis claim 5 , said dihydrolevoglucosenone being obtained by hydrogenating a levoglucosenone.11. A pure isomer of dairy-lactone of Z—R claim 1 , Z—S claim 1 , E-R or E-S conformation obtained by the method according to .12. A pure isomer of dairy-lactone according to claim 11 , wherein the pure isomer of dairy-lactone is of Z—S conformation.13. A use of a pure isomer of dairy-lactone obtained by the method according to claim 1 , as a food flavor.14. The use of a pure isomer of dairy-lactone obtained by the method according to claim 1 , as an odorant molecule to flavor a food or cosmetic product.15. A bakery product comprising a pure isomer of dairy-lactone obtained by the method according to claim 1 , to give a “buttered” note to said bakery product.16. A product based on vegetable milk or animal milk substitute having a pure isomer of dairy-lactone obtained by the method according to claim 1 , to give a “milky” note to said product. This application is a national phase entry under 35 U.S.C. § 371 of International Patent Application PCT/FR2016/050813, filed Apr. 8, 2016, designating the United States of America and published as International Patent Publication WO 2016/162646 A1 on Oct. 13, 2016, which claims the benefit under Article 8 of the Patent Cooperation Treaty to French Patent Application Serial No. 1553112 filed Apr. 10, 2015.This application is in the field of aromatic molecules, their manufacturing ...

Surfactant-Enabled Transition Metal-Catalyzed Chemistry

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions. 114.-. (canceled)16. The method of claim 15 , wherein the transition metal mediated bond formation is performed in an aqueous solvent.17. The method of claim 15 , wherein the transition metal catalyst is selected from an organo-palladium or -nickel reagent claim 15 , organo-copper or -gold reagent claim 15 , organo-rhodium or -iridium complex claim 15 , or an organo-ruthenium claim 15 , -iron claim 15 , or -osmium reagent claim 15 , wherein the catalyst is capable of promoting cross-coupling reactions claim 15 , or other reactions characteristic of catalysis by these metals claim 15 , that form a carbon-carbon claim 15 , carbon-heteroatom or carbon-hydrogen bond.18. The method of claim 15 , wherein Yis methyl.19. The method of claim 15 , wherein the solubilizing agent is selected from the group consisting of Poloxamer 188 claim 15 , Polysorbate 80 claim 15 , Polysorbate 20 claim 15 , Vit E-TPGS claim 15 , Solutol HS 15 claim 15 , PEG-40 Hydrogenated castor oil (Cremophor RH40) claim 15 , PEG-35 Castor oil (Cremophor EL) claim 15 , PEG-8-glyceryl capylate/caprate (Labrasol) claim 15 , PEG-32-glyceryl laurate (Gelucire 44/14) claim 15 , PEG-32-glyceryl palmitostearate (Gelucire 50/13); Polysorbate 85 claim 15 , polyglyceryl-6-dioleate (Caprol MPGO) claim 15 , mixtures of high and low HLB emulsifiers; sorbitan monooleate (Span 80) claim 15 , Capmul MCM claim 15 , Maisine 35-1 claim 15 , glyceryl monooleate claim 15 , glyceryl monolinoleate claim 15 , PEG-6-glyceryl oleate (Labrafil M 1944 CS) claim 15 , PEG-6-glyceryl linoleate (Labrafil M 2125 CS) claim 15 , oleic acid claim 15 , linoleic acid claim 15 , propylene glycol monocaprylate (e.g. Capmul PG-8 or Capryol ...

Method for preparing 3-trifluoromethyl chalcones

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M 1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is OR 11 or NR 12 R 13 , and R 11 , R 12 and R 13 are as defined in the disclosure. Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above.

PROCESS FOR PREPARING ARYL- AND HETEROARYLACETIC ACID DERIVATIVES

The invention relates to a process for preparing aryl- and heteroarylacetic acids and derivatives thereof by reaction of aryl or heteroaryl halides with malonic diesters in the presence of a palladium catalyst, of one or more bases and optionally of a phase transfer catalyst. This process enables the preparation of a multitude of functionalized aryl- and heteroarylacetic acids and derivatives thereof, especially also the preparation of arylacetic acids with sterically demanding substituents. 4. The process for preparing a compound of formula (III) according to claim 1 , whereAr is 1-naphthyl, 2-naphthyl, phenyl, 4-N,N-dimethylaminophenyl, 4-methylthiophenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl, 2-ethylphenyl, 4-ethoxycarbonylphenyl, 3-thienyl.5. The process for preparing a compound of formula (III) according to claim 1 , whereAr is 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 4-cyanophenyl, 4-cyano-2-methylphenyl, 3-cyanophenyl, 4-ethoxycarbonylphenyl, 4-trifluoromethylphenyl, 4-acetylphenyl, 4-nitrophenyl, 4-benzoylphenyl.6. The process for preparing a compound of formula (III) according to claim 1 , where{'sup': 6', '7, 'Rand Rare each ethyl.'}7. The process for preparing a compound of formula (III) according to claim 1 , wherein the palladium catalyst used is bis(dibenzylideneacetone)palladium claim 1 , tris(dibenzylideneacetone)dipalladium or palladium acetate.8. The process for preparing a compound of formula (III) according to claim 1 , wherein the phosphine ligand used is tri-tert-butylphosphine claim 1 , tricyclohexylphosphine claim 1 , tris(1-adamantyl)phosphine claim 1 , n-butyldi(1-adamantyl)phosphine (cataCXium® A) claim 1 , benzyldi(1-adamantyl)phosphine (cataCXium® ABn) claim 1 , 2-(di-tert-butylphosphino)biphenyl (JohnPhos) or 2-(dicyclohexylphosphino)-2′-(N claim 1 ,N-dimethylamino.9. The process for preparing a compound of ...

Method For Preparing Substituted Phenylacetic Acid Derivative

The invention belongs to the pharmaceutical manufacturing field, which relates to a novel process for the preparation of substituted phenylacetic acids derivatives, especially relates to the preparation of 2-(4-(2-oxocyclopentyl)phenyl)propanoic acid. The process for the preparation of the precursor form of loxoprofen which use 1,4-di-halobenzyl compounds or disubstituted benzyl compounds as starting material, is through the substitution reaction of cyclopentanone groups or its precursor compounds. 6. Formula G and formula Gof . Wherein the preparation method of loxoprofen include the decarboxylation step.7. According to claim 6 , the sequence of decarboxylation is from the first step to the second step and the third step.12. (canceled)13. (canceled) This application claims priority of Chinese patent application submitted to the Chinese Patent Office on Sep. 7, 2017, with the application number 201710800788.8, and entitled “Preparation Method For Substituted Phenylacetic Acid Derivatives”. All of its contents are incorporated in this application by reference.The invention belongs to the field of pharmaceutical manufacturing in reference to a preparation method of substituted phenylacetic acid derivatives, specifically relates to 2-(4-((2-oxocyclopentyl)methyl)phenyl)propanoic acid.Substituted phenylacetic acid derivatives are disclosed in U.S. Pat. No. 4,161,538, with good pharmaceutical activity of anti-inflammatory, analgesic and antipyretic. the structure is shown as follows:When A is oxygen and n=1 meanwhile and R is methyl group, in the above general formula structure, the representative substituted phenylacetic acid is loxoprofen. The structure is shown as follows:Loxoprofen is a non-steroidal anti-inflammatory type drug of with propionic acid moiety. The propionic acid derivatives drug family also include ibuprofen and naproxen et al. The loxoprofen has been launched in Brazil, Mexico and Japan in the form of sodium salt wherein honored by Sankyo. The trade ...

METHODS FOR PREPARATION OF JASMONATE COMPOUNDS

This invention relates to methods for preparation of jasmonate compounds via a salt of jasmonic acid. 2. The method of claim 1 , wherein said hydroxylheteroaryl of Step (b) is 8-hydroxyquinoline.3. The method of claim 1 , wherein said compound of formula (I) is obtained with a yield of at least 99.0% or about 94.9% claim 1 , or at a purity of about 99.6%.45.-. (canceled)6. The method of claim 1 , wherein said compound of formula (I) contains less than 3% claim 1 , 4% claim 1 , or 5% of E isomer.78.-. (canceled)9. The method of claim 1 , wherein the compound of formula (I) is obtained with a Z isomer in the amount of about 99.0%.10. (canceled)11. The method of claim 1 , wherein said acid is HCl in water.13. The method of claim 12 , wherein said base is LiOH in water.14. The method of claim 12 , wherein said organic solvent comprises ethyl acetate claim 12 , heptane claim 12 , or a mixture of ethyl acetate and n-heptane.1516.-. (canceled)17. The method of claim 12 , wherein said crude compound (8) is obtained at a purity of about 93.0%.18. (canceled)20. The method of claim 19 , wherein said solvent is a mixture of water and an organic solvent claim 19 , and claim 19 , optionally claim 19 , wherein said organic solvent is DMF.2122.-. (canceled)24. (canceled)27. The method of claim 26 , wherein said base is LiOH in water.28. The method of claim 26 , wherein said organic solvent comprises ethyl acetate claim 26 , heptane claim 26 , or a mixture of ethyl acetate and n-heptane.2930.-. (canceled)31. The method of claim 26 , wherein said crude compound (8) is obtained at a purity of about 93.0%.32. (canceled)34. The method of claim 33 , wherein said solvent is a mixture of water and an organic solvent claim 33 , and optionally claim 33 , wherein said organic solvent is DMF.3536.-. (canceled)38. (canceled) This invention relates to methods for preparation of jasmonate compounds via a salt of jasmonic acid.Jasmonates are a family of plant stress hormones, derived from ...

MIXTURES OF CANNABINOID COMPOUNDS, AND PRODUCTION AND USE THEREOF

Described are specific mixtures comprising one or more (cannabinoid) compounds of the formula (A) and/or one or more of their salts as well was methods for their production. 2. The mixture according to claim 1 , wherein the aliphatic rest of the compound of formula (A) is saturated and/or linear.5. A mixture according to claim 3 , wherein in the said formulas (A-I) claim 3 , (A-II) claim 3 , (A-III) or claim 3 , respectively claim 3 , (A-IV) each Rindependently of the meaning of each of the others of the rests Ris H or OH.7. A method of therapeutic treatment of a human or animal comprising administering to the human or animal a mixture of claim 1 , or a compound of the formula (A) claim 1 , or salt thereof.8. A method for achieving an effect selected from the group consisting of: appetizing effect claim 1 ,antiemetic effect for the inhibition of nausea and vomiting,reduction of muscular cramps and spasticities,alleviation of pain symptoms,alleviation of migraine symptoms,reduction of the intraocular pressure in the case of a glaucoma,improved sentiment,immune stimulation,antiepileptic effect, andas CB1 and/or CB2 receptor modulator;{'claim-ref': {'@idref': 'CLM-00001', 'claim 1'}, 'the method comprising administering to the human or animal a mixture of or a compound of the formula (A), or salt thereof.'}11. A method for producing a mixture according to or a compound selected from the group consisting of cyclohexylcannabidivarinolat claim 1 , hexylcannabidivarinolat and 2-hydroxyethylcannabidivarinolat or a salt thereof claim 1 , comprising the following steps: 'and', '(a) transesterification of a divarinacid ester,'}(b) reacting the divarinacid ester obtained by transesterification in step (a) with menthadienol to the corresponding compound of the formula (A).12. A method for producing THCV claim 1 , comprising the production of a mixture according to or of a compound selected from the group consisting of cyclohexylcannabidivarinolat claim 1 , ...

PD(II)-CATALYZED ENANTIOSELECTIVE C-H ARYLATION OF FREE CARBOXYLIC ACIDS

The invention includes procedures for stereoselective β-acylation of carboxylic acids having a β-carbon atom. For example, stereoselective acylation procedures include the following reactions: (I) 3. The method of wherein the Pd(II) salt is Pd(OAc).4. The method of wherein the carbonate base is NaCO claim 1 , or wherein the Ag(I) salt is AgCO claim 1 , or both.5. The method of wherein the Pd(II) salt is present at about 10 mole % claim 1 , the ligand is present at about 20 mole % claim 1 , or both.8. The method of wherein the Pd(II) salt is Pd(OAc).9. The method of wherein the carbonate base is NaCO claim 6 , or wherein the Ag(I) salt is AgCO claim 6 , or both.10. The method of wherein the Pd(II) salt is present at about 10 mole % claim 6 , the ligand is present at about 20 mole % claim 6 , or both. This application claims the priority of U.S. provisional application Ser. No. 62/659,866, filed Apr. 19, 2018, the disclosure of which is incorporated by reference herein in its entirety.This invention was made with government support under grant number GM084019 awarded by the National Institutes of Health. The government has certain rights in the invention.Desymmetrization through C—H activation holds the potential to become a broadly useful chiral technology due to the widespread presence of symmetric prochiral C(sp)—H bonds in the majority of organic molecules.Pd(II)-catalyzed enantioselective intermolecular C(sp)—H activation was recently made possible by a combination of weakly coordinating directing group and chiral bidentate ligand.This strategy was firstly demonstrated by the development of N-perfluoroaryl amide-directed enantioselective C—H cross-coupling of α-quaternary cyclopropanecarboxamides using mono-N-protected amino acids (MPAA) as the chiral ligands.Recently, chiral bidentate quinoline ligands were developed to realize enantioselective functionalization of methylene C(sp)—H bond of acyclic N-perfluoroaryl carboxamides to construct β-chiral centers,while ...

Enzymatic processes for the preparation of (±)-2-(difluoromethyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid and (±)-2-(vinyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid

Disclosed are methods of synthesizing racemic 2-(difluoromethyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acids and 2-(vinyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acids and their salts, such as the dicyclohexylamine salt. Also disclosed are methods for preparing enantioenriched (1R,2R)-1-((tert-butoxycarbonyl)amino)-2-(difluoromethyl)cyclopropane-1-carboxylic acid and esters of the same. These compounds are useful intermediates in the synthesis of viral protease inhibitors.

CATALYSIS BY METAL NANOPARTICLES DISPERSED WITHIN A HIERARCHICALLY POROUS CARBON MATERIAL

Disclosed are hierarchically porous carbon materials with a plurality of discreet nanoparticles dispersed on their carbon phase. The materials possess a continuous network of pores that spans the porous material, permitting the flow of fluids into and through the material. The porous materials can be used as heterogeneous catalysts. 1. A hierarchically porous material comprising:a) a plurality of macropores defined by a wall, wherein the macropores have a diameter of from about 0.1 μm to about 50 μm,wherein the macropores interconnect, forming a continuous network of pores that spans the porous material,wherein the walls of the macropores comprise a plurality of mesopores defined by a wall, wherein the mesopores have a diameter of from about 2 nm to about 50 nm, andwherein the walls of the macropores and mesopores comprise a continuous carbon phase; andb) a plurality of discreet nanoparticles dispersed on the carbon phase of the macropores and mesopores.2. The material of claim 1 , wherein the material is a monolith.3. The material of claim 1 , wherein the material is a particle.4. The material of claim 1 , wherein the macropores have a diameter of from about 0.5 μm to about 30 μm.5. The material of claim 1 , wherein the mesopores having a diameter of from about 2 nm to about 15 nm thereby resulting in a porous material with hierarchical pores.6. The material of claim 1 , wherein the nanoparticles comprise a catalytically active metal claim 1 , metal oxide claim 1 , or combinations thereof.7. The material of claim 6 , wherein the metal claim 6 , metal oxide claim 6 , or combinations thereof comprise a metal selected from the group consisting of Ti claim 6 , V claim 6 , Cr claim 6 , Mn claim 6 , Fe claim 6 , Co claim 6 , Ni claim 6 , Cu claim 6 , Zr claim 6 , Nb claim 6 , Mo claim 6 , Tc claim 6 , Ru claim 6 , Rh claim 6 , Pd claim 6 , Ag claim 6 , Hf claim 6 , Ta claim 6 , W claim 6 , Re claim 6 , Os claim 6 , Ir claim 6 , Pt claim 6 , Au claim 6 , La claim 6 , Ce ...

Spiroketal-Based C2-Symmetric Scaffold For Asymmetric Catalysis

Provided herein is a compound of formula (I): 4. The compound of claim 1 , wherein at least one X is OH.5. (canceled)6. The compound of claim 1 , wherein at least one X is PAr.7. (canceled)8. The compound of claim 1 , wherein at least one X is OPAr.9. (canceled)10. The compound of claim 1 , wherein at least one X is P(O)Ar.1112.-. (canceled)13. The compound of claim 6 , wherein Ar comprises phenyl.14. The compound of claim 1 , wherein both X together form OPNR′.1518.-. (canceled)19. The compound of claim 14 , wherein R′ is methyl.2022.-. (canceled)23. The compound of claim 1 , wherein R is ethyl.2428.-. (canceled)29. The compound of claim 1 , wherein at least one R is 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N claim 1 , O claim 1 , and S.3034.-. (canceled)36. A catalyst comprising the compound of formula (I) according to and a transition metal.37. The catalyst of claim 36 , wherein the transition metal comprises iridium claim 36 , palladium claim 36 , rhodium claim 36 , platinum claim 36 , copper claim 36 , nickel claim 36 , cobalt claim 36 , or gold.38. A method of preparing the catalyst of comprising admixing the compound of formula (I) and the transition metal to form the catalyst.39. (canceled)40. The method of claim 38 , wherein the transition metal comprises [Ir(COD)Cl] claim 38 , [Pd(allyl)Cl] claim 38 , or Pd(dba).41. The method of claim 38 , wherein the compound of formula (I) and the transition metal are provided in a molar ratio of about 6:1 to 1:1.42. A method comprising:{'claim-ref': {'@idref': 'CLM-00036', 'claim 36'}, 'admixing a first reactant, a second reactant, and the catalyst of under conditions sufficient to allow reaction of the first reactant and the second reactant to form a reaction product, wherein the reaction product comprises a chiral center and the reaction produces an enantiomeric excess (ee) of the reaction product.'}43. The method of claim 42 , wherein the reaction comprises a hydroarylation ...

SURFACE ACTIVE AGENTS DERIVED FROM BIODIESEL-BASED ALKYLATED AROMATIC COMPOUNDS

A surface active agent comprising an arylated methyl ester of a fatty acid, or mixture of fatty acids, derived from biodiesel or a triglyceride source is disclosed. The fatty acid mixture is condensed to methyl esters and alkylated with aromatic substituents under Friedel-Crafts conditions. The alkylated methyl esters may be alkoxylated using a catalyst derived from fatty acids, alkaline earth salts, and strong acids. The resulting nonionic surfactant may also be sulfonated to produce one class of anionic surfactants. The alkylated methyl esters may also be directly sulfonated to produce another class of anionic surfactants. 1. A method of making a chemical composition , comprising:forming an unsaturated fatty acid methyl ester composition by subjecting an unsaturated fatty acid to an esterification process;forming an aromatic alkylate from the unsaturated fatty acid methyl ester composition by performing an aromatic alkylation process on the unsaturated fatty acid methyl ester composition; andethoxylating the aromatic alkylate.2. The method of claim 1 , wherein forming the aromatic alkylate comprises reacting the unsaturated fatty acid methyl ester composition with benzene in the presence of an ionic liquid catalyst.3. The method of claim 2 , wherein ethoxylating the aromatic alkylate comprises contacting the aromatic alkylate with an ethylene oxide in the presence of a catalyst derived from a fatty acid claim 2 , an alkaline earth salt claim 2 , and a strong acid.4. The method of claim 3 , wherein the catalyst is further derived from a glycol.5. The method of claim 1 , further comprising sulfonating the ethoxylated aromatic alkylate.6. The method of claim 5 , wherein sulfonating the ethoxylated aromatic alkylate comprises contacting the ethoxylated aromatic alkylate with a sulfonic acid.7. The method of claim 1 , wherein the unsaturated fatty acid is selected from a natural oil claim 1 , a biodiesel precursor claim 1 , or combinations thereof.8. The method of ...

Low system memory detection

Methods, systems, and computer readable media may be operable to facilitate an anticipation of an execution of a process termination tool. An allocation stall counter may be queried at a certain frequency, and from the query of the allocation stall counter, a number of allocation stall counter increments occurring over a certain duration of time may be determined. If the number of allocation stall counter increments is greater than a threshold, a determination may be made that system memory is running low and that an execution of a process termination tool is imminent. In response to the determination that system memory is running low, a flag indicating that system memory is running low may be set, and one or more programs, in response to reading the flag, may free memory that is not necessary or required for execution.

PROCESS FOR THE PRODUCTION OF ETHYLENICALLY UNSATURATED CARBOXYLIC ACIDS OR ESTERS

The present invention relates to a process for the production of an ethylenically unsaturated carboxylic acid or ester, preferably α,β ethylenically unsaturated carboxylic acids or esters, by the liquid phase reaction of formaldehyde or a suitable source thereof with a non-cyclic carboxylic acid ester in the presence of a basic metal salt. 1. A process for production of an ethylenically unsaturated carboxylic acid or ester , unsaturated carboxylic by a liquid phase reaction of formaldehyde or a suitable source thereof with a non-cyclic carboxylic acid ester in the presence of a basic metal salt.2. The process according to claim 1 , wherein the basic metal salt is a group I or a group II metal salt.3. The process according to claim 1 , wherein the basic metal salt is selected from group I or group II metal oxides claim 1 , hydroxides claim 1 , carbonates claim 1 , hydrogen carbonates claim 1 , methyl carbonates claim 1 , alkoxides claim 1 , fluorides and phosphates.4. The process according to claim 1 , wherein the basic metal salt is selected from potassium oxide claim 1 , caesium oxide claim 1 , sodium oxide claim 1 , rubidium oxide claim 1 , barium oxide claim 1 , potassium hydroxide claim 1 , caesium hydroxide claim 1 , sodium hydroxide claim 1 , rubidium hydroxide claim 1 , barium hydroxide claim 1 , potassium phosphate claim 1 , caesium phosphate claim 1 , sodium phosphate claim 1 , rubidium phosphate claim 1 , barium phosphate claim 1 , sodium methoxide claim 1 , potassium methoxide claim 1 , rubidium methoxide claim 1 , sodium t-butoxide claim 1 , potassium t-butoxide claim 1 , rubidium t-butoxide claim 1 , caesium t-butoxide claim 1 , sodium fluoride claim 1 , potassium fluoride claim 1 , rubidium fluoride claim 1 , caesium fluoride claim 1 , potassium carbonate claim 1 , caesium carbonate claim 1 , sodium carbonate claim 1 , rubidium carbonate claim 1 , barium carbonate claim 1 , potassium hydrogen carbonate claim 1 , sodium hydrogen carbonate claim 1 , ...

METHOD OF PREPARING SUBSTITUTED BICYCLO[1.1.1] PENTANES

A process for the preparation of a class of molecules, namely bicyclo[1.1.1]pentanes and derivatives thereof by reaction of [1.1.1]propellane with a variety of reagents under irradiation and/or in the presence of radical initiators to obtain bicyclo[1.1.1]pentanes asymmetrically substituted at position 1 and 3, which are useful as intermediates for the preparation of asymmetrically 1,3-disubstituted bicyclo[1.1.1]pentane derivatives and various physiologically active substances or materials containing these structures. 2. A one-step process according to claim 1 , wherein X is halogen claim 1 , preferably Cl.5. A process according to claim 3 , wherein the reaction steps to obtain a compound of Formula V from a compound of Formula II are performed (a) in a batch system and/or (b) in a flow system.6. A process according to claim 4 , wherein the reaction steps to obtain a compound of Formula I from a compound of Formula IV are performed (a) in a batch system and/or (b) in a flow system.7. A process according to claim 4 , wherein the reaction steps to obtain a compound of V from a compound of Formula IV are performed (a) in a batch system and/or (b) in a flow system.8. A process according to wherein the step of reacting [1.1.1]propellane of formula II with a compound of formula III is carried out under irradiation.9. A process according to wherein the step of reacting [1.1.1]propellane of formula II with a compound of formula III is carried out in the presence of a radical initiator.14. A process according to wherein Z is C.15. A process according to wherein Z is S.16. A process according to wherein Z is S(═O).17. A process according to wherein Y represents R—C(═O)— or ROC(═O)— claim 1 , wherein Ris saturated linear or branched —(C-C)alkyl or aryl. The invention relates to a new and efficient process for the preparation of a class of molecules, namely bicyclo[1.1.1]pentanes and derivatives thereof by a one-step reaction of [1.1.1]propellane with a variety of reagents ...

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I 128-. (canceled)30. The method of claim 29 , wherein subscript y is 7.31. The method of claim 29 , wherein Ris H claim 29 , Ris methyl claim 29 , Ris acetyl claim 29 , subscript y is 7 claim 29 , and subscript z is 3.34. The method of claim 29 , wherein the metathesis catalyst is of the formula LL′AA′M═CRRor LL′AA′M═(C═)CRR claim 29 , whereinM is ruthenium;L and L′ are each independently any neutral electron donor ligand and preferably selected from phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibnite, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, thioether, or heterocyclic carbenes; and{'sub': 1', '20', '1', '20', '2', '20', '1', '20', '1', '20', '1', '20', '1', '5', '1', '5', '1', '5', '1', '5, 'A and A′ are anionic ligands independently selected from halogen, hydrogen, C-Calkyl, aryl, C-Calkoxide, aryloxide, C-Calkoxycarbonyl, arylcarboxylate, C-Ccarboxylate, arylsulfonyl, C-Calkylsulfonyl, C-Calkylsulfinyl; each ligand optionally being substituted with C-Calkyl, halogen, C-Calkoxy; or with a phenyl group that is optionally substituted with halogen, C-Calkyl, or C-Calkoxy; and A and A′ together may optionally comprise a bidentate ligand; and'}{'sub': b', 'c', '1', '20', '1', '20', '1', '20', '1', '20', '1', '20', '1', '20', '1', '20', 'b', 'c', '1', '5', '1', '5', '1', '5', '1', '5, 'Rand Rare independently selected from hydrogen, C-Calkyl, aryl, C-Ccarboxylate, C-Calkoxy, aryloxy, C-Calkoxycarbonyl, C-Calkylthio, C-Calkylsulfonyl and C-Calkylsulfinyl, each of Rand Roptionally substituted with C-Calkyl, halogen, C-Calkoxy or with a phenyl group that is optionally substituted with halogen, C-Calkyl, or C-Calkoxy.'}38. The method of claim 37 , wherein the olefin is a linear C-Colefin claim 37 , the metathesis reaction part is a Δ-unsaturated fatty acid ...

Method for producing fullerene derivative

(in formula (1), C* are each carbon atoms adjacent to each other for forming a fullerene skeleton, A is a linking group having 1-4 carbon atoms for forming a ring structure with two C*, in which a portion thereof may be a substituted or condensed group).

METHOD FOR PREPARING AZETIDINONE COMPOUND AND INTERMEDIATE OF AZETIDINONE COMPOUND

Disclosed is a new method for preparing an azetidinone compound represented by formula (I). The carboxylic ketoester represented by formula (II) serves as the raw material and is subjected to Grignard addition, stereoselective dehydration, ester group reduction, hydroxyl group protection, addition with imine after condensation with a chiral auxiliary, cyclization and deprotection to obtain the compound represented by formula (I). The present invention has advantages of easily available raw material, a few synthetic steps, simple operation, high yield, good stereoselectivity and low cost, and can be used for industrial production. 3. The method according to claim 1 , characterized in that in step (a) or (ab) claim 1 , the alcoholic hydroxyl protecting group Ris selected from the following groups: acetyl claim 1 , substituted or unsubstituted benzoyl claim 1 , preferably substituted benzoyl; wherein the substituted is substituted by halogen claim 1 , alkyl or nitro claim 1 , preferably substituted by nitro claim 1 , more preferably substituted by nitro at the 3-position; the molar ratio of the compound V to the hydroxyl protecting agent in step (a) is 1:1.0˜3.0 claim 1 , preferably 1:1.2˜2.3 claim 1 , or the molar ratio of the compound V to the hydroxyl protecting agent in step (ab) is 1:1.0˜3.0 claim 1 , preferably 1:1.0˜1.5; and the solvent of the reaction in step (a) or the solvent of the reaction of synthesizing compound of formula VI from the compound of formula V in step (ab) is selected from N claim 1 ,N-dimethylformamide (DMF) claim 1 , N claim 1 ,N-dimethylacetamide (DMA) claim 1 , dimethylsulfoxide (DMSO) claim 1 , 1 claim 1 ,3-dimethylpropyleneurea (DMPU) or hexamethylphosphoramide (HMPA) claim 1 , preferably N claim 1 ,N-dimethylacetamide (DMA).4. The method according to claim 1 , characterized in that in step (b) or step (ab) claim 1 , the acylating agent used for forming the mixed anhydride is selected from pivaloyl chloride claim 1 , 3-nitrobenzoyl ...

METHOD FOR FORMING CARBON-CARBON BOND

A method for forming a carbon-carbon bond, wherein a reaction is performed by filling a platinum group metal-supported catalyst into a filling container, and passing a raw material liquid through the platinum group metal-supported catalyst in a continuous circulation manner, and wherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger formed of a continuous framework phase and a continuous pore phase. 1. A method for forming a carbon-carbon bond to form a carbon-carbon bond by performing (1) reaction of an aromatic halide with an organoboron compound , (2) reaction of an aromatic halide with a compound having a terminal alkynyl group , or (3) a reaction of an aromatic halide with a compound having an alkenyl group ,wherein the carbon-carbon bond-forming reaction is performed by introducing a raw material liquid (i) containing the aromatic halide and the organoboron compound, a raw material liquid (ii) containing the aromatic halide and the compound having a terminal alkynyl group, or a raw material liquid (iii) containing the aromatic halide and the compound having an alkenyl group, through an introduction path of a filling container filled with a platinum group metal-supported catalyst, into the filling container, passing the raw material liquid through the platinum group metal-supported catalyst, and discharging the reaction liquid from a discharge path of the filling container, andwherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger, and the non-particulate organic porous ion exchanger is formed of a continuous framework phase and a continuous pore phase; has a ...

Process Involving Cross Metathesis of Olefins

A method of forming a macrocyclic musk compound comprising the steps of: — 1. A method of forming a macrocyclic musk compound comprising the steps of: —i) cross-metathesizing a first olefin and a second olefin in the presence of a homogeneous transition metal catalyst comprising an alkylidene ligand, to form a statistical mixture of a hetero-dimer intermediate of said first and second terminal olefin, and homo-dimersii) separating the hetero-dimer from the statistical mixture of hetero- and homo-dimersiii) and cyclizing the hetero-dimer intermediate to form the macrocyclic musk compound.7. A method according to claim 1 , wherein the first olefin and second olefin are reacted in a 1:x molar ratio to produce a ratio of hetero-dimer:first homo-dimer:second homo-dimer of 2x:1:1x.8. A method according to claim 1 , wherein the hetero-dimer is formed in admixture with a protected alcohol homo-dimer and a carboxylic acid ester homo-dimer.9. A method according to wherein the mixture of protected alcohol hetero-dimer and each carboxylic acid ester homo-dimer is formed in a molar ratio of 2:1:1.10. A method according to claim 1 , wherein the hetero-dimer is separated from the homo-dimers by distillation at a temperature of 100 to 220 degrees centigrade and a pressure of 1 to 10 mbar.11. A method according to claim 1 , wherein the homo-dimers are recycled by metathesis with ethylene to regenerate the first and second olefins.12. A method according to wherein the homo-dimers are treated with ethylene gas at a pressure of 1 bar to 20 bar.13. A method according to claim 1 , wherein the hetero-dimer is cyclised by trans-esterification.14. A method according to wherein claim 13 , if the hetero-dimer contains a protected alcohol group claim 13 , it is first de-protected by hydrolysis before being subjected to cyclisation by tran-esterification.15. A method of forming E/Z 9-ambrettolide according to the method according to .16. A method of forming E/Z 9-ambrettolide according to claim ...

SYNTHESIS OF INTERMEDIATES FOR PRODUCING PROSTACYCLIN DERIVATIVES

The present disclosure provides regioselective methods for synthesizing intermediates useful in making prostacyclin derivatives, such as treprostinil. 2. The method of claim 1 , wherein said solution is heated at a temperature ranging from 175° C. to 195° C.3. The method of claim 1 , wherein X is hydrogen or an alkoxy group.4. The method of claim 3 , wherein the organic solvent comprises at least one of triglyme claim 3 , N-methylpyrrolidinone claim 3 , tetradecane claim 3 , tetrahydronaphthalene claim 3 , Dowtherm claim 3 , p-chlorophenol claim 3 , 1 claim 3 ,2-dichlorobenzene claim 3 , and diphenyl ether.7. The method of claim 6 , further comprising forming from the compound of formula 5 treprostinil using a process comprising Pauson-Khand cyclization.8. The method of claim 6 , wherein Ris benzyl or substituted benzyl.9. The method of claim 6 , wherein Ris CHCOOR claim 6 , wherein Ris Calkyl.10. The method of claim 1 , wherein X is OR claim 1 , where Ris Calkyl; unsubstituted or substituted aryl; or unsubstituted or substituted benzyl.11. The method of claim 10 , wherein Ris methyl.12. The method of claim 10 , wherein Ris ethyl.15. The method of claim 14 , further comprising forming from the compound of formula 5 treprostinil using a process comprising Pauson-Khand cyclization.16. The method of claim 14 , wherein Ris benzyl or substituted benzyl.17. The method of claim 14 , wherein Ris CHCOOR.19. The method of claim 18 , further comprising forming from the compound of formula 11 treprostinil using a process comprising Pauson-Khand cyclization.20. The method of claim 18 , wherein Ris Calkyl.21. The method of claim 18 , wherein Ris a phenolic protecting group.22. The method of claim 21 , wherein Ris benzyl. The present application claims priority to U.S. provisional application No. 62/066,009 filed Oct. 20, 2014, which is incorporated herein by reference in its entirety.The present application generally relates to chemical synthetic methods and in particular, to ...

Process for the production of methyl methacrylate

The invention includes a process of producing methyl methacrylate or derivatives thereof is described. The process includes the steps of converting 2-butanone to methyl propionate using a Baeyer-Villiger monooxygenase, and treating the methyl propionate produced to obtain methyl methacrylate or derivatives thereof. A method of preparing polymers or copolymers of methyl methacrylate or its derivatives is also described.

Synthesis of New Anti-Inflammatory Compound

According to embodiments of present disclosure, a method to produce a compound of Formula 19 is provided. Using this method, the compound of Formula 19 may be produced effectively. 3. The method of claim 2 , wherein the contacting is performed in THF.4. The method of claim 2 , wherein the contacting is performed in the presence of in zinc chloride.5. The method of claim 2 , wherein a molar amount of Bis(triphenylphosphine) palladium(II) chloride is about 2% to about 8% of that of compound of Formula 2.6. The method of claim 2 , wherein the contacting is carried out under a temperature ranging from room temperature to about reflux temperature.8. The method of claim 7 , wherein the concentration of DIBAL-D is 1.2M to 2.0M.10. The method of claim 9 , wherein the contacting of ethyl propiolate with lithium bromide base is performed in a solvent comprising acetic acid and acetonitrile claim 9 , and the volume ratio of acetic acid to acetonitrile is 1:2˜2:1.11. The method of claim 1 , wherein the contacting of ethyl propiolate with lithium bromide base is performed under a temperature ranging from about 40° C. to about a reflux temperature.13. The method of claim 12 , wherein the contacting is performed under a temperature from room temperature to about reflux temperature.14. The method of claim 12 , wherein the contacting is performed in toluene. The present invention relates generally to the synthesis of Lipoxin derivate. In particular it relates to the preparation of Lipoxin derivate and intermediates for the preparation of Lipoxin derivate.Lipoxins are a series of anti-inflammatory mediators. Lipoxins are short lived endogenously produced nonclassic eicosanoids whose appearance in inflammation signals the resolution of inflammation. They are abbreviated as LX, an acronym for lipoxygenase (LO) interaction products. At present two lipoxins have been identified; lipoxin A4 (LXA4) and lipoxin B4 (LXB4).Lipoxins were first described by Serhan, Hamberg and Samuelsson in ...

GLUCAGON RECEPTOR ANTAGONISTS

Provided herein are solid state forms of compounds, including enantiomerically pure forms thereof, and pharmaceutically acceptable salts or co-crystals and prodrugs thereof which have glucagon receptor antagonist or inverse agonist activity. Further, provided herein are pharmaceutical compositions and methods of treating, preventing, ameliorating, delaying the time to onset or reducing the risk for the development or progression of at least one condition, disease, or disorder for which one or more glucagon receptor antagonist is indicated, including Type I and II diabetes, insulin resistance, hyperglycemia, ketoacidosis, or ketosis. 1. A crystalline form selected from the group consisting of a crystalline form of sodium (R)-2-(4-(2-(4′-(tert-butyl)-[1 ,1′-biphenyl]-4-yl)-3-oxo-3-((2′ ,4′ ,6′-trimethyl-[1 ,1′-biphenyl]-4-yl)amino)propyl)benzamido)ethane-1-sulfonate characterized as Form A , a crystalline form of calcium (R)-2-(4-(2-(4′-(tert-butyl)-[1 ,1′-biphenyl]-4-yl)-3-oxo-3-((2′ ,4′ ,6′-trimethyl-[1 ,1′-biphenyl]-4-yl)amino)propyl)benzamido)ethane-1-sulfonate characterized as Form B , and a crystalline form of potassium (R)-2-(4-(2-(4′-(tert-butyl)-[1 ,1′-biphenyl]-4-yl)-3-oxo-3-((2′ ,4′ ,6′-trimethyl-[1 ,1′-biphenyl]-4-yl)amino)propyl)benzamido)ethane-1-sulfonate characterized as Form C.2. Form A of claim 1 , wherein Form A is characterized by one or more peaks in an X-ray powder diffraction pattern claim 1 , wherein the one or more peaks is selected from the group consisting of a peak from about 4.2 to about 4.8 degrees claim 1 , a peak from about 6.7 to about 7.1 degrees claim 1 , a peak from about 9.0 to about 9.4 degrees claim 1 , a peak from about 10.8 to about 11.2 degrees claim 1 , a peak from about 11.1 to about 11.5 degrees claim 1 , a peak from about 11.7 to about 12.1 degrees claim 1 , a peak from about 13.5 to about 13.9 degrees claim 1 , a peak from about 21.2 to about 21.6 degrees claim 1 , and a peak from about 23.6 to about 24.0 degrees claim 1 ...

Process for preparing di-substituted succinates

The invention relates to a process for preparing (2,3) disubstituted succinates that allows (2,3) disubstituted succinates to be obtained in good purity and with acceptable reaction yields. The (2) and (3) substitutions may be the same or different. The process comprises reacting a haloacetate with a malonic acid ester into a tricarboxylate, which is further reacted to a (2,3) disubstituted tricarboxylate, hydrolysed, decarboxylated and optionally esterified. Esterified (2,3) disubstituted succinic esters may be used as internal donor in Ziegler-Natta type catalysts for the polymerisation of olefins.

METHOD FOR PRODUCTION OF 3-HYDROXYPROPAN-1-ONE COMPOUND, METHOD FOR PRODUCTION OF 2-PROPEN-1-ONE COMPOUND AND METHOD FOR PRODUCTION OF ISOXAZOLINE COMPOUND

There is provided a novel intermediate for producing pesticides. A method for producing the compound of Formula (3) comprises reacting an aromatic ketone compound of Formula (4) and a substituted acetophenone compound of Formula (5) as starting raw materials in an organic solvent or water in the presence or absence of an additive in the presence of a base in a suspended state. A method may comprise dehydrating the compound of Formula (3). A method for producing compound (2) in one step comprises reacting compound (4) and compound (5) to obtain compound (3). Further, a method for producing an isoxazoline compound of Formula (1) comprises reacting compound (2) and a hydroxylamine in an aliphatic or an aromatic hydrocarbon solvent which is optionally substituted by a halogen atom by adding an additive selected from a phase-transfer catalyst, a C-Calcohol and an aprotic polar solvent in the presence of a base and water. 2. The method according to claim 1 , wherein the solvent is an organic solvent and the reaction is conducted in the absence of the additive.3. The method according to claim 1 , wherein the solvent is water and the reaction is conducted in the presence of a water-soluble organic solvent as the additive.4. The method according to claim 1 , wherein the solvent is water and the reaction is conducted in the presence of a surfactant as the additive. This is a Division of application Ser. No. 12/452,347 filed Dec. 28, 2009, which in turn is a National Phase application of PCT/JP2008/061771 filed on Jun. 27, 2008. The disclosures of the prior applications are hereby incorporated by reference herein in their entirety.The present invention relates to a method for producing a 3-hydroxypropan-1-one compound, a 2-propen-1-one compound and an isoxazoline compound which are useful for functional materials such as medical drugs, agricultural chemicals or electronic materials or production intermediates thereof.Methods for producing an isoxazoline compound from a 1,3-bis ...

MANUFACTURE OF 1-SUBSTITUTED METHYLIDENE COMPOUNDS

Compounds of the formula (I) wherein R, A are certain substituents, Y is an ester group, a nitrile group or an amido group and Z is O, S or N′R, and which compounds are, for example, useful as intermediates for pyrazole fungicides, can be prepared by the reaction of a compound of formula R—C(O)—CHY, with an orthoformate HC—(OR)in the presence of a base, especially in the presence of an amine, e.g. triethylamine 2. The method of wherein Ris an organic substituent selected from the group consisting of C1 to C5 alkyl.3. The method of wherein Z is O.4. The method of anyone of wherein Y is C(O)ORwherein Ris a C1 to C5 alkyl group.5. The method of wherein Ris selected from the group consisting of chloromethyl claim 1 , dichloromethyl claim 1 , trichloromethyl claim 1 , fluoromethyl claim 1 , difluoromethyl claim 1 , trifluoromethyl claim 1 , chlorobromomethyl claim 1 , chlorofluoromethyl claim 1 , chlorodifluoromethyl claim 1 , fluorodichloromethyl claim 1 , 1-fluoroethyl claim 1 , 2-fluoroethyl claim 1 , 2 claim 1 ,2-difluoroethyl claim 1 , 2 claim 1 ,2 claim 1 ,2-trifluoroethyl claim 1 , 1-chloroethyl claim 1 , 2 claim 1 ,2-dichloroethyl claim 1 , 1 claim 1 ,2-dichloroethyl claim 1 , 2-chlorofluoroethyl claim 1 , 2-chloro-2 claim 1 ,2-difluoroethyl claim 1 , 2 claim 1 ,2-dichloro-2-fluoroethyl claim 1 , 2 claim 1 ,2 claim 1 ,2-trichloroethyl claim 1 , pentafluoroethyl and 1 claim 1 ,1 claim 1 ,1-trifluoro-prop-2-yl.6. The method of wherein Ris CClF.7. The method of wherein R claim 1 , R claim 1 , R claim 1 , R claim 1 , Rand Rare C1 to C5 alkyl.8. The method of wherein the base is NHor an organic base.9. The method of wherein the organic base is selected from primary claim 1 , secondary and tertiary amines.10. The method of wherein the base is selected from amines having the formula (IV) claim 1 , NRRR claim 1 , wherein R claim 1 , Rand Rare the same or different and are H or C1 to C10 alkyl with the proviso that at least one of R claim 1 , Rand Ris not H; or wherein at ...

COMPLEXES

A palladium(II) complex of formula (1) or a palladium(II) complex of formula (3). 2. A palladium(II) complex according to claim 1 , wherein E is P.3. A palladium(II) complex according to claim 1 , wherein Rand Rare independently selected from the group consisting of substituted and unsubstituted straight-chain alkyl claim 1 , substituted and unsubstituted branched-chain alkyl claim 1 , substituted and unsubstituted cycloalkyl claim 1 , substituted and unsubstituted aryl claim 1 , and substituted and unsubstituted heteroaryl wherein the heteroatoms are independently selected from sulfur claim 1 , nitrogen and oxygen.4. A palladium(II) complex according to claim 1 , wherein R claim 1 , R claim 1 , Rand Rare independently selected from the group consisting of —H claim 1 , substituted and unsubstituted straight-chain alkyl claim 1 , substituted and unsubstituted branched-chain alkyl claim 1 , substituted and unsubstituted cycloalkyl claim 1 , substituted and unsubstituted alkoxy claim 1 , substituted and unsubstituted aryl claim 1 , substituted and unsubstituted heteroaryl claim 1 , substituted and unsubstituted —N(alkyl)(wherein the alkyl groups may be the same or different and are independently selected from straight-chain or branched-chain groups) claim 1 , substituted and unsubstituted —N(cycloalkyl)(wherein the cycloalkyl groups may be the same or different) claim 1 , substituted and unsubstituted —N(aryl)(wherein the aryl groups may be the same or different) claim 1 , substituted and unsubstituted —N(heteroaryl)(wherein the heteroaryl groups may be the same or different) and substituted and unsubstituted heterocycloalkyl groups.5. A palladium(II) complex according to claim 4 , wherein each of R claim 4 , R claim 4 , Rand Rare —H.6. A palladium(II) complex according to claim 4 , wherein each of R claim 4 , R claim 4 , Rand Rare independently straight-chain alkyl groups claim 4 , preferably -Me.7. A palladium(II) complex according to claim 1 , wherein two of R claim ...

Improved process for preparing substituted crotonic acids

A process to prepare a compound of Formula (I) wherein R 3 , R 4 and R 5 are each selected independently from hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxyl, and wherein the alkyl, alkenyl, alkynyl, and alkoxyl may be optionally substituted with one or more halogen, alkyl, alkenyl, alkynyl, and alkoxyl.

METHOD FOR PREPARING AZETIDINONE COMPOUND AND INTERMEDIATE OF AZETIDINONE COMPOUND

Disclosed is a new method for preparing an azetidinone compound represented by formula (I). The carboxylic ketoester represented by formula (II) serves as the raw material and is subjected to Grignard addition, stereoselective dehydration, ester group reduction, hydroxyl group protection, addition with imine after condensation with a chiral auxiliary, cyclization and deprotection to obtain the compound represented by formula (I). The present invention has advantages of easily available raw material, a few synthetic steps, simple operation, high yield, good stereoselectivity and low cost, and can be used for industrial production. 3. The method according to claim 2 , characterized in that a solvent of the reaction is selected from dichloromethane claim 2 , tetrahydrofuran claim 2 , toluene or dioxane claim 2 , preferably toluene.4. The method according to claim 2 , characterized in that the reducing agent is diisobutylaluminium hydride (DIBAH).5. The method according to claim 2 , characterized in that a molar ratio of the compound of formula IV to the reducing agent is 1:2.5˜5.0 claim 2 , preferably 1:3.0˜4.0.8. The method according to claim 7 , characterized in that the dehydrating agent is selected from concentrated sulfuric acid claim 7 , p-toluenesulfonic acid claim 7 , phosphoric acid claim 7 , triflic anhydride or methanesulfonic acid claim 7 , preferably triflic anhydride; a molar ratio of the compound of formula III to the dehydrating agent is 1:1.0˜3.0 claim 7 , preferably 1:1.0˜1.5; and a solvent of the reaction is selected from dichloromethane or toluene claim 7 , preferably dichloromethane.910-. (canceled)13. The method according to claim 12 , wherein 4-fluorophenyl magnesium halide is 4-fluorophenyl magnesium bromide; a molar ratio of the compound of formula II to 4-fluorophenyl magnesium halide is 1:1.0˜5.0 claim 12 , preferably 1:1.1˜3.0; and a temperature of the reaction is controlled between −78° C.˜−5° C. claim 12 , preferably −50° C.˜−10° C.1415-. ...

SUBSTITUTED QUINOLINYLCYCLOHEXYLPROPANAMIDE COMPOUNDS AND IMPROVED METHODS FOR THEIR PREPARATION

The disclosure is directed to improved methods for preparing substituted quinolinylcyclohexylpropanamide compounds. 116-. (canceled)1922-. (canceled) This application claims the benefit of U.S. Provisional Application No. 62/527,821, filed Jun. 30, 2017, U.S. Provisional Application No. 62/527,835, filed Jun. 30, 2017, and U.S. Provisional Application No. 62/649,155, filed Mar. 28, 2018, the entireties of which are incorporated by reference herein.The disclosure is directed to improved methods for preparing substituted quinolinylcyclohexylpropanamide compounds.Indoleamine 2,3-dioxygenase (IDO; also known as IDO1) is an IFN-γ target gene that plays a role in immunomodulation. IDO plays a major role in immune regulation, and its immunosuppressive function manifests in several manners. A pathophysiological link exists between IDO and cancer. Disruption of immune homeostasis is intimately involved with tumor growth and progression, and the production of IDO in the tumor microenvironment appears to aid in tumor growth and metastasis. Moreover, increased levels of IDO activity are associated with a variety of different tumors (Brandacher, G. et al., 12(4):1144-1151 (Feb. 15, 2006)). In addition to cancer, IDO has been implicated in, among other conditions, immunosuppression, chronic infections, and autoimmune diseases or disorders (e.g., rheumatoid arthritis).Substituted quinolinylcyclohexylpropanamide pharmaceutical compounds that inhibit IDO and are useful for the treatment of cancer have been previously described. See, e.g., WO2016/073770. Improved methods of making such compounds, which reduce production costs and improve production safety, are, therefore, needed.The disclosure is directed to methods of making compounds of formula I, or stereoisomers thereof:contacting the compound of formula III, or a stereoisomer thereof, with a suitable organic acid, in a suitable aqueous solvent, for a time and at a temperature sufficient for hydrolysis and decarboxylation and to ...

NEW PROCESS FOR THE PREPARATION OF 2-CYCLOPENTYL-6-METHOXY-ISONICOTINIC ACID

The present invention relates to new processes for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid, which is a useful intermediate for the synthesis of pyridine-4-yl derivatives as immunomodulating agent. Moreover, the present invention also relates to new intermediates used in those processes. 4. The process according to claim 3 , wherein R is ethyl.8. The process according to claim 5 , further comprising the reaction of compound (6) with phosphorous oxychloride (POCl) claim 5 , followed by treatment with methanol claim 5 , to give methyl 2-chloro-6-cyclopentylisonicotinate (8).10. The compound ethyl 2-cyclopentyl-5-cyano-6-hydroxyisonicotinate or a salt thereof.11. The compound 2-cyclopentyl-6-hydroxyisonicotinic acid or a salt thereof.12. The compound methyl 2-cyclopentyl-6-hydroxyisonicotinate or a salt thereof.13. The compound methyl 2-chloro-6-cyclopentylisonicotinate or a salt thereof.15. The process according to for preparing a compound selected from the group consisting of:(S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol;(R)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol;ethanesulfonic acid {2-chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]-oxadiazol-3-yl]-6-methyl-phenyl}-amide;N—((S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;N—((S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-N-methyl-acetamide;N— {2-chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-methane sulfonamide;(S)-3-{2-chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol;N—((S)-3-{2-chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2- ...

Preparation of sitagliptin intermediates

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

PROCESS FOR PREPARING TAPINAROF

The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same. 3. A process for preparing a compound of claim 1 , comprising crystallizing a compound of Formula (I) using methanol and water.4. The process of claim 3 , wherein the process comprises seeding.5. The compound of prepared by a process comprising crystallizing a compound of Formula (I) using methanol and water.6. A pharmaceutical composition comprising a compound of and a pharmaceutically acceptable excipient.7. A pharmaceutical composition comprising a compound of and a pharmaceutically acceptable excipient. The present application is a Continuation of U.S. application Ser. No. 16/849,346, filed Apr. 15, 2020, which is a Continuation of U.S. application Ser. No. 16/189,268, filed Nov. 13, 2018, now U.S. Pat. No. 10,647,649, which claims benefit of and priority to U.S. Provisional No. 62/584,192 entitled “PROCESS,” filed Nov. 10, 2017, the contents of which are herein incorporated by reference in their entirety.Some embodiments of the present invention provides a processes for the preparation of the compound of Formula (I) or a salt thereof and to novel intermediates used thereinSome embodiments of the present invention describe a compound of Formula (IIa) or a salt thereofand processes for preparing same.Some embodiments of the present invention describe a compound of Formula (IVa) or a salt thereofand processes for preparing same.Some embodiments of the present invention describe a compound of Formula (V) or a salt thereofand processes for preparing same.Some embodiments of the present invention describe a ...

Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside

The invention relates to processes for preparing (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside and compositions comprising the same.

PROCESS FOR PREPARING SUBSTITUTED CROTONIC ACIDS

A process to prepare a compound of Formula (I) 119-. (canceled)21. The process of claim 20 , wherein the base of step a) is an amine.22. The process of claim 20 , wherein the reagent of step b) is an acid or a base.23. The process of claim 22 , wherein the base is sodium hydroxide claim 22 , lithium hydroxide or potassium hydroxide.25. The process of claim 24 , wherein the steps i) claim 24 , ii) claim 24 , a) and b) are conducted without isolation of the intermediate compounds of Formulas IV claim 24 , V or VI.26. The process of claim 24 , wherein the base of step i) is LiHMDS claim 24 , sodium hydride claim 24 , LDA claim 24 , KOtBu or NaOEt.27. The process of claim 24 , wherein the reducing agent of step ii) is lithium borohydride claim 24 , sodium borohydride claim 24 , disiamylborane claim 24 , hydrogen with platinum (IV) oxide claim 24 , hydrogen with palladium/carbon or zinc borohydride.28. The process of claim 20 , wherein at least one of R claim 20 , Rand Ris halogen.29. The process of claim 28 , wherein the halogen is bromine claim 28 , chlorine or fluorine.30. The process of claim 20 , wherein at least one of R claim 20 , Rand Ris alkyl.31. The process of claim 20 , wherein Ris CHand Rand Rare both fluorine.32. The process of claim 20 , wherein Ris ethyl.33. The process of claim 24 , wherein Ris methyl or ethyl.34. The process of claim 20 , wherein Ris Cl and Rand Rare both fluorine.35. The process of claim 20 , wherein Ris Br and Rand Rare both fluorine.36. The process of claim 20 , wherein Ris CF claim 20 , Ris CHO and Ris fluorine.37. The process of claim 20 , wherein Ris CHand Rand Rare both chlorine.38. The process of claim 20 , wherein Ris CF claim 20 , Ris chlorine and Ris fluorine.39. The process of claim 21 , wherein the amine is triethylamine. WO2012/041872 discloses novel N-heteroaryl compounds that are useful as medicaments. This patent application also discloses the dehydration of ethyl 4,4,5,5-tetrafluoro-3-hydroxy-pentanoate to ethyl (E)-4, ...

METHOD FOR PURIFYING CANNABINOID COMPOUNDS

The present invention relates to methods for purifying one or two cannabinoid compounds using simulated moving bed chromatography, wherein the cannabinoid compound(s) is/are obtained in the extract and/or the raffmate with the total amount of isomeric impurities being below detection level. In particular, the present invention relates to methods for the purification of cannabidiol, trans-(−)-delta-9-tetrahydrocannabinol, cannabidivarin, trans-(−)-delta-9-tetrahydrocannabivarin and cannabigerol which have been obtained by enantiopure synthesis. 1. A method for purifying one or two cannabinoid compounds comprising:i) providing a mixture comprising at least one cannabinoid compound obtained by enantiopure synthesis and one or more of its isomers and optionally one or more further organic compounds, and a) continuously feeding the mixture of step i) through a feed port into a simulated moving bed chromatographic apparatus comprising at least four columns connected in series and containing a stationary phase, and', 'b) continuously feeding eluant into the apparatus through an eluant port, and', 'c) continuously withdrawing the extract through an extract port, and', 'wherein the extract and/or the raffinate respectively comprise(s) one purified cannabinoid compound and wherein the extract and/or the raffinate comprising one purified cannabinoid compound comprise(s) less than 100 ppm in total of any isomer(s) of the purified cannabinoid compound present in step i).', 'd) continuously withdrawing the raffinate through a raffinate port,'}], 'ii) simultaneously,'}2. The method according to claim 1 , additionally comprising:iii) subjecting the extract and/or the raffinate comprising one purified cannabinoid compound to one, two or more further extraction step(s), wherein the extract and/or the raffinate respectively obtained in step iii) comprise(s) one purified cannabinoid compound and less than 100 ppm in total of any further organic compound(s) present in step i).3. The ...

FE/CU-MEDIATED KETONE SYNTHESIS

Provided herein are methods for preparing ketone-containing organic molecules. The methods are based on novel iron/copper-mediated (“Fe/Cu-mediated”) coupling reactions. The Fe/Cu-mediated coupling reaction can be used in the preparation of complex molecules, such as halichondrins and analogs thereof. In particular, the Fe/Cu-mediated ketolization reactions described herein are useful in the preparation of intermediates en route to halichondrins. 8. The method of any one of - , wherein the step of coupling is carried out in the presence of copper and iron.9. The method of any one of - , wherein the iron source is iron (II) or iron (III).10. The method of any one of - , wherein the iron source is an iron complex.11. The method of claim 10 , wherein the iron complex is of the formula Fe(ligand).13. The method of any one of - claim 10 , wherein the iron complex is Fe(TMHD) claim 10 , Fe(DBM) claim 10 , or Fe(acac).14. The method of claim 10 , wherein the iron complex is of the formula Fe(X)(ligand) claim 10 , wherein each instance of X is independently halogen; and “ligand” is two phosphine ligands or a bisphosphine ligand.15. The method of claim 14 , wherein the iron complex is selected from the group consisting of Fe(Br)(dppb) claim 14 , Fe(Cl)(dppb) claim 14 , Fe(Br)(SciOPP) claim 14 , Fe(Cl)(SciOPP) claim 14 , FeBr(dppe) claim 14 , and FeCl(dppe).16. The method of claim 10 , wherein the iron complex is FeBr(PPh)or FeCl(PPh).17. The method of any one of - claim 10 , wherein the iron is present in a catalytic amount.18. The method of claim 17 , wherein the iron is present in from 1-20 mol %.19. The method of claim 18 , wherein the iron is present in approximately 5 mol %.20. The method of claim 18 , wherein the iron is present in approximately 10 mol %.21. The method of claim 18 , wherein the iron is present in approximately 15 mol %.22. The method of any one of - claim 18 , wherein the copper source is copper (I) or copper (II).23. The method of any one of - claim ...

METHYLIDENE MALONATE PROCESS

An improved process for the production of methylidene malonates is attained by use of select iminium salt reactants. 2. The method of wherein Rand Rare each H and Rand Rare each independently alkyl claim 1 , or alkenyl.3. The method of wherein X is a halogen claim 1 , a non-nucleophilic anion claim 1 , and/or acidic anion.4. The method of wherein X is a halogen claim 1 , a carboxylate or a sulfonate.5. The method of wherein X is selected from chloride claim 1 , bromide claim 1 , iodide claim 1 , AsF claim 1 , SbF claim 1 , PF claim 1 , BF claim 1 , CHSO claim 1 , CFSO claim 1 , benzenesulfonate claim 1 , para-toluenesulfonate claim 1 , acetate claim 1 , propionate claim 1 , isobutyrate claim 1 , pivalate claim 1 , sufate claim 1 , bisulfate claim 1 , perchlorate claim 1 , SbCl claim 1 , SbCl claim 1 , and SnCl.7. The method of wherein Rand Rare both hydrocarbon and/or heterohydrocarbon groups and represent a Cto Clinear or branched alkyl group claim 6 , a Cto Calicyclic group claim 6 , a Cto Calkenyl group claim 6 , or a Cto Calkynyl group claim 6 , either or both of which may be substituted with or contain an ether claim 6 , epoxide claim 6 , halo claim 6 , ester claim 6 , cyano claim 6 , aldehyde claim 6 , keto or aryl group.8. The method of wherein both Rand Rare hydrocarbon or heterohydrocarbon groups wherein at least one contains an ester linkage.9. The method of wherein at least one of the Rand Rgroups is of the formula:{'br': None, 'sub': 2', 'n, 'sup': '3', '—(CH)—COOR'}{'sup': '3', 'sub': 1', '17, 'wherein Ris a Cto Chydrocarbon or heterohydrocarbon group, the latter having one or more nitrogen, halogen, or oxygen atoms, and n is an integer of from 1 to 5.'}10. The method of wherein the malonic acid ester is a diester and a least one of Rand Ris a group is of the formula:{'br': None, 'sub': 2', '2, 'sup': '3', '—(CH)—COOR'}{'sup': '3', 'sub': 1', '17, 'wherein Ris independently a Cto Chydrocarbon or heterohydrocarbon group, the latter having one or more ...

A PROCESS FOR THE PREPARATION OF ALKYL 3-DIFLUOROMETHYL-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE AND ITS ANALOGS

The disclosure provides a process for the preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate and its analogs. The process includes a reaction workup method for Claisen condensation, wherein the enolate salt is acidified after removing remaining starting material and byproducts such as, ethanol and excessive ethyl acetate. The process also includes a method for completely drying alkyl difluoroacetoacetate and its analogs before use in the next step by reacting trialkyl orthoformate with the residual water. The process includes using NaCOand/or KCOto promote the ring-closure reaction to produce the alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate. The process also includes effectively removing the regioisomer, alkyl 3-difluoromethyl-2-methyl-1H-pyrazole-4-carboxylate formed as a byproduct of the ring closure by a precipitation in a mixed solvent system and thereby eliminating the need for recrystallization of the final product. 5. The process of any one of to , additionally comprising: removing residual water from the compound of Formula XVI by hydrolysis with trialkyl orthoformate prior to coupling the compound of Formula XVI with the trialkyl orthoformate.6. The process of claim 5 , wherein the hydrolysis is catalyzed with an acid.7. The process of claim 6 , wherein the hydrolysis is catalyzed by a strong protic acid selected from a group consisting of HSO claim 6 , HNO claim 6 , HCl claim 6 , HBr claim 6 , HI claim 6 , TFA claim 6 , HPO claim 6 , p-TSA and MSA.8. The process of any one of to claim 6 , wherein the trialkyl orthoformate is a tri(C-C)alkyl orthoformate.9. The process of any one of to claim 6 , wherein the acidification of the enolate metal salt of Formula XV is conducted between about −20° C. to about 30° C.10. The process of any one of to claim 6 , wherein the compound of Formula XVI is extracted by a water-immiscible solvent claim 6 , a low water-miscible organic solvent claim 6 , or a mixture of a water-immiscible ...

Method for providing an active ruthenium catalyst solution for the transvinylation of carboxylic acids

The invention relates to a method for providing a ruthenium catalyst solution which is active during the transvinylation of a surfactant vinyl ester with a surfactant carboxylic acid, comprising an Ru metal concentration of more than 0.5 wt. % based on the total weight of the ruthenium catalyst solution. The invention is characterized in that a) at least one ruthenium (III) halogenide with at least one inorganic or organic base, at least one surfactant vinyl ester, and at least one surfactant carboxylic acid is reacted at a temperature of 70° C. to 170° C.; b) the molar ratio of surfactant vinyl ester to surfactant carboxylic acid is 1:1.8 to 1.8:1; and c) the ruthenium (III) halogenide is used in a quantity of >0.5 wt. % of Ru metal based on the total weight of the surfactant vinyl ester and surfactant carboxylic acid.

Synthesis of intermediates for producing prostacyclin derivatives

The present disclosure provides regioselective methods for synthesizing intermediates useful in making prostacyclin derivatives, such as treprostinil.

Process for synthesis of ezetimibe and intermediates used in said process

A process for the production of ezetimibe and intermediates used in said process are disclosed. A kind of Morita-Baylis-Hillman adduct can be altered to chiral carboxylic acid derivatives of β-arylamino α-methylene with high activity and selectivity by means of ally lamination reaction, and the above carboxylic acid derivatives of β-arylamino α-methylene can be altered to the chiral intermediates of ezetimibe by means of simple conversion and further synthesized into the chiral drug ezetimibe. The synthesis route introduces chirality through the use of a chiral catalysis method, thereby avoiding the use of the chiral auxiliary oxazolidinone; and the route is economical and eco-friendly.

SYNTHESIS OF METHYLENE MALONATES SUBSTANTIALLY FREE OF IMPURITIES

The present invention provides improved methods for the chemical synthesis of methylene malonates using the Knovenagel synthesis reaction. The method of the invention provides for improved methylene malonates by significantly reducing or eliminating the formation of alternative and/or deleterious side products, significantly reducing or eliminating unwanted consumption of methylene malonates, and significantly reducing or eliminating the degradation of methylene malonates. These advantages result in methylene malonates, which upon recovery, are of higher quality, greater purity, improved yield and possess overall improved performance characteristics (e.g., improved cure speed, retention of cure speed, improved shelf-life and/or stability). 158-. (canceled)59. A method of making a methylene malonate monomer comprising:(a) reacting a malonic acid ester with a source of formaldehyde in the presence of an acidic or basic catalyst and optionally in the presence of an acidic or non-acidic solvent, to form a reaction complex;(b) optionally, inactivating the catalyst; and(c) recovering methylene malonate monomer from the reaction complex.60. The method according to claim 59 , wherein inactivating the catalyst comprises forming an insoluble precipitate of the catalyst and removing the precipitate from the reaction mixture.61. The method according to claim 60 , wherein the precipitate is formed by reducing the solubility of the catalyst in the reaction mixture.62. The method according to further comprising:(d) minimizing the recovery of volatile latent acid forming impurities from the reaction complex.63. The method according to claim 62 , wherein the step of minimizing the recovery of volatile latent acid forming impurities comprises:(a) adding to the reaction mixture water and an acid having a pKa range of −8 to 5;(b) adding to the reaction mixture a sterically hindered organic acid; or(c) adding to the reaction mixture a non-volatile organic acid, or any combination of (a ...

Process for ruthenium-catalysed transvinylation of carboxylic acids

A process for selective transvinylation of a reactant carboxylic acid with a reactant vinyl ester to give a product vinyl ester and the corresponding acid of the reactant vinyl ester in the presence of one or more ruthenium catalysts, wherein a) the reactant vinyl ester, the reactant carboxylic acid and the ruthenium catalyst are supplied to a reactor, wherein b) the molar ratio of reactant vinyl ester to reactant carboxylic acid is 1:3 to 3:1, and c) the transvinylation reaction is conducted, d) on completion of the transvinylation reaction, the reactant vinyl ester and the corresponding acid are separated from the reaction mixture by distillation, e) the product vinyl ester is separated by distillation from the bottom product of the distillation, and f) the remaining reaction mixture is recycled into the reactor.

N-heterocyclic carbene type palladium catalyst and its preparation method as well as applications

The present invention relates to an n-heterocyclic carbene (NHC) type palladium catalyst and its preparation method as well as applications. Its preparation process is as below: select glyoxal as the raw material to synthesize glyoxaldiimine in the presence of Lewis acid or Bronsted acid, and then react with paraformaldehyde to get the NHC type ligand. Use palladium (II) to react with the compound containing carbon-nitrogen double bonds to get palladium (II) cyclic dimer; make the palladium cyclic dimer and the NHC type ligand coordinated to get the NHC type palladium catalyst. The palladium catalyst with a brand new structure according to the present invention, boasts high activity and multi-purpose. In addition, it shows excellent reaction activity in a lot of catalytic-coupling reactions including Suzuki-Miyaura, Heck, Buchwald-Hartwig, Kumada-Tamao-Corriu, Sonogashira, Negishi and α-ketone arylation reactions, and some reactions even can be carried out with the presence of an extremely low concentration of catalyst, exhibiting favorable industrialization prospect.

PHOTOLABILE PRO-FRAGRANCES

A method for producing photo-cleavable fragrance pre-cursors is described, which includes potential stereoselective method steps, agents containing the fragrance pre-cursors and the use of the fragrance pre-cursors for prolonging the scent impression in the agent and on surfaces treated with said agent. 2. The method according to claim 1 , wherein the ketone of the general formula (II) has at least one semicyclic or exocyclic double bond.3. The method according to claim 1 , wherein the bridging part —R7-Q-R6 of the ketone of the general formula (II) is a hydrocarbon.4. The method according to claim 1 , wherein the ketone of the general formula (II) is selected from the group consisting of (+)-dihydrocarvone claim 1 , (+)-isodihydrocarvone claim 1 , (−)-dihydrocarvone claim 1 , (−)-isodihydrocarvone claim 1 , or mixtures thereof.5. The method according to claim 1 , wherein the radicals Rand Rof the phosphonate of the general formula (III) claim 1 , in each case independently of one another claim 1 , are methoxy claim 1 , ethoxy claim 1 , n-propoxy claim 1 , i-propoxy radicals claim 1 , or combinations thereof.6. The method according to claim 1 , wherein the radical Rof the phosphonate of the general formula (III) is a methyl claim 1 , ethyl claim 1 , n-propyl claim 1 , i-propyl claim 1 , n-butyl claim 1 , sec-butyl claim 1 , i-butyl claim 1 , or t-butyl radical.7. The method according to claim 1 , wherein the reduction in method step d) takes place in the presence of an organic catalyst.8. The method according to claim 1 , wherein the reduction in method step d) is stereoselective.9. The method according to claim 1 , wherein the reduction in method step d) takes place in the presence of a chiral catalyst.10. The method according to claim 1 , wherein the reduction in method step d) takes place in the presence of a chiral imidazolidinone.16. The agent of claim 15 , wherein the agent is selected from the group consisting ofa washing agent, a cleaning agent, a cosmetic ...

IMPROVED PROCESS FOR THE PREPARATION OF PRALATREXATE

An improved process for the preparation of Pralatrexate which is less hazardous. The invention further relates to novel intermediates and process thereof useful for the preparation of Pralatrexate. The present invention also relates to a substantially pure Pralatrexate and a process for obtaining the same in high yield. 2. A process of claim 1 , wherein the alkylating agent of step (a) is propargyl bromide.3. A process of claim 1 , wherein the base of step (a) is potassium carbonate.4. A process of claim 1 , wherein the phase transfer catalyst of step (a) is tetra butyl ammonium iodide.5. A process of claim 1 , wherein the base of step (b) is sodium hydride.6. A process of claim 1 , wherein the suitable solvent of step (b) is dimethylacetamide.7. A process of claim 1 , wherein the acid of step (b) is selected from the group comprising of HCl or HBr.8. A process of claim 1 , wherein the base of step (c) is potassium hydroxide.9. A process of claim 1 , wherein the base of step (d) is dicyclohexylamine and n is 2.10. A process of claim 1 , wherein the suitable solvent of step (e) is dimethylacetamide or dimethylsulfoxide.11. A process of claim 1 , wherein the suitable base of step (e) is sodium hydroxide.12. A process of claim 1 , wherein the activating agent of step (g) is 1-hydroxybenztriazole.13. A process of claim 1 , wherein the suitable dehydrating agent of step (g) is 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride.14. A process of claim 1 , wherein the suitable base of step (h) is sodium hydroxide.16. The compound of claim 15 , wherein X is HBr.18. The compound of claim 17 , wherein Y is dicyclohexylamine and n is 2.20. The compound of claim 19 , wherein M is selected from the group comprising of sodium claim 19 , lithium and potassium.21. A process for obtaining substantially pure Pralatrexate of Formula (I) comprising the steps ofa) contacting Pralatrexate with a mixture of alcohol and halogenated hydrocarbon to obtain a mixture;b) stirring the ...

FE/CU-MEDIATED KETONE SYNTHESIS

Provided herein are methods for preparing ketone-containing organic molecules. The methods are based on novel iron/copper-mediated (“Fe/Cu-mediated”) coupling reactions. The Fe/Cu-mediated coupling reaction can be used in the preparation of complex molecules, such as halichondrins and analogs thereof. In particular, the Fe/Cu-mediated ketolization reactions described herein are useful in the preparation of intermediates en route to halichondrins. 8. The method of any one of - , wherein the step of coupling is carried out in the presence of copper and iron.9. The method of any one of - , wherein the iron source is iron (II) or iron (III).10. The method of any one of - , wherein the iron source is an iron complex.11. The method of claim 10 , wherein the iron complex is of the formula Fe(ligand).13. The method of any one of - claim 10 , wherein the iron complex is Fe(TMHD) claim 10 , Fe(DBM) claim 10 , or Fe(acac).14. The method of claim 10 , wherein the iron complex is of the formula Fe(X)(ligand) claim 10 , wherein each instance of X is independently halogen; and “ligand” is two phosphine ligands or a bisphosphine ligand.15. The method of claim 14 , wherein the iron complex is selected from the group consisting of Fe(Br)(dppb) claim 14 , Fe(Cl)(dppb) claim 14 , Fe(Br)(SciOPP) claim 14 , Fe(Cl)(SciOPP) claim 14 , FeBr(dppe) claim 14 , and FeCl(dppe).16. The method of claim 10 , wherein the iron complex is FeBr(PPh)or FeCl(PPh).17. The method of any one of - claim 10 , wherein the iron is present in a catalytic amount.18. The method of claim 17 , wherein the iron is present in from 1-20 mol %.19. The method of claim 18 , wherein the iron is present in approximately 5 mol %.20. The method of claim 18 , wherein the iron is present in approximately 10 mol %.21. The method of claim 18 , wherein the iron is present in approximately 15 mol %.22. The method of any one of - claim 18 , wherein the copper source is copper (I) or copper (II).23. The method of any one of - claim ...

Process for crossed claisen condensation reactions promoted by lithium amide in liquid ammonia

The present invention provides a use of lithium amide in liquid ammonia as a base to produce an enolate from at least one ester starting material in a crossed Claisen condensation reaction, wherein at least one ester starting material is a β-hydroxy ester. Also provided is a method of producing lithium amide in situ for use in a crossed Claisen condensation reaction, wherein lithium is added to liquid ammonia, followed by an electron transfer agent, as well as a method of carrying out a crossed Claisen condensation reaction using an ester starting material and a β-hydroxy ester, using lithium amide in liquid ammonia produced in situ.

SYNTHESIS OF LONG-CHAIN UNSATURATED FATTY ACID BY CHEMICAL REACTION OF CARBON CHAIN EXTENSION

A method of chemically extending a carbon chain of an unsaturated fatty acid for conversion into a different unsaturated fatty acid has been reported. The present invention shortens reaction steps of conventional methods, and completes a carbon chain extending reaction in a shorter time. The present invention provides a method of extending a carbon chain of an unsaturated fatty acid by two carbons, comprising steps of four stages including a short-path conversion reaction of an unsaturated fatty chain obtained from an unsaturated fatty acid into a malonic ester derivative, and heating of the malonic ester derivative to reflux in a lower fatty acid solution. The method of the present invention can complete a carbon chain extending reaction in a shorter time. 1. A method of extending a carbon chain of an unsaturated fatty acid by 2 carbons , comprising reacting a malonic ester derivative of an unsaturated fatty chain that is produced by reduction of the unsaturated fatty acid or an unsaturated fatty acid ester thereof , with a lower fatty acid.2. The method of claim 1 , wherein the unsaturated fatty acid is an unsaturated fatty acid with 16-24 carbons.3. The method of claim 1 , wherein the unsaturated fatty acid is selected from the group consisting of linoleic acid claim 1 , linolenic acid claim 1 , arachidonic acid claim 1 , stearidonic acid claim 1 , icosatetraenoic acid claim 1 , icosapentaenoic acid claim 1 , docosapentaenoic acid claim 1 , and docosahexaenoic acid.4. The method of claim 1 , wherein the malonic ester derivative is a derivative selected from the group consisting of a diethyl malonate derivative claim 1 , dimethyl malonate derivative claim 1 , diisopropyl malonate derivative claim 1 , and dibutyl malonate derivative.5. The method of claim 1 , wherein the malonic ester derivative of the unsaturated fatty chain is produced by: a formation reaction of an unsaturated alcohol by reduction of the unsaturated fatty acid or an ester thereof; a formation ...

METHOD FOR PRODUCING ORGANIC COMPOUND

The present invention addresses the problem of providing a method for producing an organic compound by a phase transfer catalysis reaction using a forced thin-film microreactor. In the present invention, at least two types of fluid, which are a first fluid and a second fluid are used; the first fluid and the second fluid are not miscible with each other; at least the first fluid thereamong includes one or two items selected from the three items of an organic compound, a reactant, and a phase transfer catalyst; from among the fluids other than the first fluid, at least the second fluid includes at least one item from among the items not selected from the three items; the overall first fluid and second fluid contain all of the three items; and each of the fluids merged 1. A method for producing an organic compound , whereinat least two fluids, a first fluid and a second fluid, are used,the first fluid and the second fluid are immiscible with each other,of the two fluids, at least the first fluid contains one or more entities selected from three entities selected from an organic compound, a reacting agent, and a phase-transfer catalyst,of the fluids other than the first fluid, at least the second fluid contains at least one entity not selected from the three entities,the first fluid and the second fluid as the whole contains the three entities,the first fluid and the second fluid are converged by introducing into a thin film fluid formed between processing surfaces which are disposed in a position they are faced with each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, thereby conducting a phase-transfer catalysis reaction in the thin film fluid, andof the first fluid and the second fluid, a fluid containing at least the phase-transfer catalyst is prepared, before it is introduced into the processing surfaces, such that the phase-transfer catalyst contained in the first fluid and/or the second ...

Method for Producing Fluorine-Containing Cyclopropane Carboxylic Acid Compound

The present invention provides an industrially applicable method for production of a fluorine-containing cyclopropane carboxylic acid compound useful as an intermediate for pharmaceutical and agrichemical products. A fluorine-containing cyclopropane monoester is obtained by: forming a fluorine-containing cyclic sulfate with the use of a fluorine-containing dial compound and sulfuryl fluoride (as a cyclic sulfuric esterification step); reacting the fluorine-containing cyclic sulfate with a malonic diester, thereby forming a fluorine-containing cyclopropane diester (as a cyclopropanation step); and hydrolyzing the fluorine-containing cyclopropane diester (as a hydrolysis step). The fluorine-containing cyclopropane carboxylic acid compound, such as fluorine-containing cyclopropane monoester or its salt, can be obtained with high chemical and optical purity by mixing the fluorine-containing cyclopropane monoester with an amine and subjecting the resulting salt of the fluorine-containing cyclopropane monoester and amine to recrystallization purification. 2. The method according to claim 1 , wherein Ris a difluoromethyl group or a trifluoromethyl group.3. The method according to claim 1 , wherein the fluorine-containing diol compound is reacted with the sulfuryl fluoride in a temperature range of −50 to +50° C.4. The method according to claim 1 , wherein the sulfuryl fluoride is used in an amount of 0.7 to 4.0 equivalents.6. The method according to claim 5 , wherein the inorganic base is an alkali metal claim 5 , an alkali metal hydride claim 5 , an alkaline earth metal hydride claim 5 , an alkali metal hydroxide or an alkaline earth metal hydroxide.7. The method according to claim 5 , wherein the fluorine-containing cyclic sulfate of the general formula [2] and the malonic diester of the general formula [3] are added into a solvent containing the inorganic base.9. The method according to claim 8 , wherein the hydrolysis is performed at a temperature of −30 to +40° C. The ...

Method for producing fluorinated compound

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1):wherein R1 represents an organic group, RA represents hydrogen or fluorine, R4a represents hydrogen or an organic group, R4b represents hydrogen or an organic group, R5a represents hydrogen or an organic group, R5b represents hydrogen or an organic group, and R2 represents hydrogen or an organic group; R2 is optionally connected to R4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):wherein X1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):wherein X2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

METHYLIDENE MALONATE PROCESS

Novel improved processes for the production and isolation of methylidene malonates via direct and indirect adduct processes. 2. The process of wherein the flash distillation is conducted in a still pot or vessel and at least a portion of a separation phase polymerization inhibitor is added to the still pot or vessel prior to initiating flash distillation claim 1 , said separation phase polymerization inhibitor comprising at least one liquid phase anionic polymerization inhibitor claim 1 , alone or in combination with a free radical polymerization inhibitor.3. The process of wherein at least a portion of the same or a different separation phase polymerization inhibitor is also added to the collection vessel for the methylidene malonate prior to initiating flash distillation.4. The process of wherein additional separation phase stabilizer is added to the methylidene malonate recovered from the flash distillation process.5. The process of wherein the anionic polymerization inhibitor of the separation phase polymerization inhibitor comprises at least one primary anionic polymerization inhibitor claim 2 , at least one secondary anionic polymerization inhibitor or a combination thereof.6. The process of wherein the methylene malonate is recovered from the vapor phase in a collection vessel and at least a portion of a separation phase polymerization inhibitor comprising at least one anionic polymerization inhibitor and claim 1 , optionally claim 1 , a free radical polymerization inhibitor is added to the collection vessel prior to initiating flash distillation.7. The process of wherein additional separation phase stabilizer is added to the methylidene malonate recovered from the flash distillation process.8. The process of wherein the anionic polymerization inhibitor of the separation phase polymerization inhibitor comprises at least one primary anionic polymerization inhibitor claim 6 , at least one secondary anionic polymerization inhibitor or a combination thereof.9. ...

Metalloprotease inhibitors, methods for producing same, and therapeutic uses thereof

The invention relates to new α-vinyl carbonylated compounds corresponding to general formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 and Y are as defined in claim 1 , their isomers, their diastereoisomers and acid addition salts or a pharmaceutically acceptable base. The invention also relates to a method for producing said compounds (I). It further relates to the use of said compounds (I) as selective metalloprotease inhibitors, especially matrix metalloproteases 12 (MMP-12) and/or 9 (MMP-9). The compounds (I) are particularly useful for the prevention and/or treatment of chronic obstructive pulmonary disease (COPD), particularly emphysema induced by cigarette smoke.

PROCESSES AND INTERMEDIATES FOR PREPARING alpha,omega-DICARBOXYLIC ACID-TERMINATED DIALKANE ETHERS

The present disclosure provides a process for the preparation of compounds of formula (III), 124.-. (canceled)36. The process of claim 34 , wherein each Ris methyl claim 34 , each Ris methyl and each m is 1.37. The process of claim 35 , wherein each Ris methyl claim 35 , each Ris methyl and each m is 1.40. The process of claim 38 , further comprising:allowing the ethanolic mixture to cool to room temperature;diluting the ethanolic mixture with methyl t-butyl ether;allowing compound (4) to precipitate from the ethanolic mixture; andfiltering compound (4) from the ethanolic mixture to provide a filtered compound (4).41. The process of claim 39 , further comprising:allowing the ethanolic mixture to cool to room temperature;diluting the ethanolic mixture with methyl t-butyl ether;allowing compound (4) to precipitate from the ethanolic mixture; andfiltering compound (4) from the ethanolic mixture to provide a filtered compound (4).42. A process for making a hydrate of compound (4) claim 39 , comprising:{'claim-ref': {'@idref': 'CLM-00040', 'claim 40'}, 'performing the process of ;'}drying the filtered compound (4); andhydrating the filtered compound (4) to provide the hydrate of compound (4).43. A process for making a hydrate of compound (4) claim 39 , comprising:{'claim-ref': {'@idref': 'CLM-00041', 'claim 41'}, 'performing the process of ;'}drying the filtered compound (4); andhydrating the filtered compound (4) to provide the hydrate of compound (4).44. The process of claim 42 , wherein the hydrating is performed at 100° C.45. The process of claim 43 , wherein the hydrating is performed at 100° C.47. The process of claim 46 , wherein Mis Caand x is 1 claim 46 , or Mis Kand x is 2; and [{'sup': 1', '+, '(a) potassium hydroxide to provide the compound of formula (50) wherein Mis K and x is 2, or'}, {'sup': 1', '2+, '(b) calcium hydroxide or calcium oxide to provide the compound of formula (50) wherein Mis Caand x is 1.'}], 'comprising hydrolyzing the compound of formula ...

FLUOROALKYLATING AGENT

Problem to be Solved 2. The agent according to claim 1 , wherein{'sup': '1', 'Ris a C1 to C4 perfluoroalkyl group;'}{'sup': 2', '3, 'Rand Rare each independently a C1 to C4 alkyl group or a phenyl group;'}{'sup': 1', '2', '3', '4, 'Y, Y, Yand Yare each independently'}a hydrogen atom, a halogen atom, a nitro group, a cyano group,a C1 to C4 alkyl group or a C1 to C4 haloalkyl group; and{'sup': −', '−', '−', '−, 'X is Cl, Br, I,'}{'sub': '4', 'sup': '−', 'BF,'}{'sub': 3', '3, 'sup': '−', 'CFSO,'}{'sub': 3', '3', '3', '2', '5', '3, 'sup': −', '−', '−, 'HOSO, CHOSO or CHOSO.'}3. The agent according to claim 1 , wherein{'sup': '1', 'Ris a trifluoromethyl group or a pentafluoroethyl group;'}{'sup': 2', '3, 'Rand Rare each independently a methyl group, an ethyl group or a phenyl group;'}{'sup': 1', '2', '3', '4, 'Y, Y, Yand Yare each independently a hydrogen atom, a chlorine atom or a nitro group; and'}{'sup': −', '−', '−', '−, 'X is Cl, Br, I,'}{'sub': '4', 'sup': '−', 'BF,'}{'sub': 3', '3, 'sup': '−', 'CFSO,'}{'sub': 3', '3', '3', '2', '5', '3, 'sup': −', '−', '−, 'HOSO, CHOSO or CHOSO.'}4. The agent according to claim 1 , wherein{'sup': '1', 'Ris a trifluoromethyl group;'}{'sup': 2', '3, 'Rand Rare each a methyl group;'}{'sup': 1', '2', '3', '4, 'Y, Y, Yand Yare each a hydrogen atom; and'}{'sup': −', '−, 'sub': 3', '3, 'X is CHOSO.'}6. The method according to claim 5 , wherein{'sup': '1', 'Ris a C1 to C4 perfluoroalkyl group;'}{'sup': 2', '3, 'Rand Rare each independently a C1 to C4 alkyl group or a phenyl group;'}{'sup': 1', '2', '3', '4, 'Y, Y, Yand Yare each independently'}a hydrogen atom, a halogen atom, a nitro group, a cyano group,a C1 to C4 alkyl group or a C1 to C4 haloalkyl group; and{'sup': −', '−', '−', '−, 'X is Cl, Br, I,'}{'sub': '4', 'sup': '−', 'BF,'}{'sub': 3', '3, 'sup': '−', 'CFSO,'}{'sub': 3', '3', '3', '2', '5', '3, 'sup': −', '−', '−, 'HOSO, CHOSO or CHOSO.'}7. The method according to claim 5 , wherein{'sup': '1', 'Ris a trifluoromethyl group or a ...